During my relationship with a former partner, I pulled away from friends so that I wouldn’t have to open up about what was really going on—or, at the very least, I’d leave out the worst parts so that it never seemed as unhealthy as it was. 

“When things are good, it’s amazing,” I’d say, not admitting that our bad moments were nearly unbearable, sometimes too traumatic to recall. To be honest, this didn’t work anyway. They still knew we didn’t have a good relationship, except now, they felt hurt by me trying to mislead them. 

I loved him. I thought I was protecting us—protecting him from being disliked by the people closest to me. If I shared that he spent two hours yelling at me for ruining his day or called me names while I cried, my friends would never want to hang out with us again. 

It’s not uncommon for people to look to their friends for approval of their relationship. Studies show that their support—or lack of it—affects our partnerships, no matter how much we might like the person we’re dating. What may be less discussed is how our friendships can become strained when we stay in unhealthy relationships.

During times when my ex and I were technically broken up, I made up stories about where I was going and who I was hanging out with so that no one would know I was running back to him. 

I remember toeing the line with my best friend, telling her thoroughly edited stories while trying to convince her that she just didn’t know him like I did. My cortisol levels during those years were pretty high, and I began having nightmares that she was upset with me. (In real life, she and I never fight.) 

My subconscious knew. 

I recalled all of this while chatting with a friend—let’s call her Sarah—this weekend, telling her about the new man I’ve been dating. “Unhealthy relationships can lead to unhealthy friendships,” she said, gently giving me a glimpse into how she might have felt when I was with my ex. 

When friends feel the need to lie about their partner, it ultimately chips away at the trust that you have built with each other over the months or years you’ve been close. Suddenly, you’re having to remember which lie you told which person. The first lie has to tie into the second and fifth and so on… for eternity.

I don’t think I really grasped until recently that part of the healing process after a toxic relationship involves rebuilding trust with friends. It’s difficult to admit that my actions—my choice to stay with someone who wasn’t right for me—came at the expense of my friendships. I was hurt in that relationship, but so were my friends.

Now, as I navigate my new relationship, I have to take accountability and make sure I don’t make that mistake again. If I need to fabricate the truth in order for my friends to like him, then chances are this isn’t a healthy situation. (Obviously, our friends will have different dealbreakers and priorities for what they’re looking for, but I’m assuming your confidants will want what’s best for you and won’t lead you astray with their own agendas.) 

Telling Sarah about my new partner, I realized, is easy. Fun. I don’t need to lie or stretch the truth. There’s no withholding. I feel happy as I tell her about how he plans intentional date nights and calm as I discuss times we’ve had to work through difficult conversations. 

My friends who have met him like him—without me having to do damage control on his reputation. It’s freeing. And, man, does it feel good to have nothing to hide.

If you’re joining me on this dating journey, I’m hoping that my missteps will help you avoid a few of your own—especially when it comes to the people in your life who love you the most. Moving on from a bad relationship is one thing; having to rebuild trust with those who’ve been by your side for years is a whole other beast. And really, what one person is worth giving up your friends for? Hint: No one.

If you’re new to Unhinged, catch up on all the dating chats you’ve missed here and follow along at @monicles and @sandiegomag on Instagram to know when a new article drops each week.

Sign-up now for the Unhinged newsletter for exclusive content, Q&As with Nicolle, and subscriber-only meet-ups!

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(To get caught up, you can read part one of our conversation here.)

Mateo Hoke (MH): Tell me about your personal readiness for a relationship right now.

Nicolle Monico (NM): It’s weird to say, but I feel like I like myself again. I feel like I’m a catch, and I don’t know if I could have always said that. I have qualities I am proud of, and I think that’s crucial for dating. Loving yourself matters because it shows. I’ve done a lot of work to discover what I need and to say it’s okay to need those things.

The last four years have been particularly hard, which pushed me to really understand and embrace my needs. I know what I can offer and what I’m not willing to give up. This clarity has given me a strong sense of self-worth. I am not afraid to ask for what I deserve in a relationship.

MH: What do you think are the real keys to being “ready” for love and commitment if you don’t feel that security in and love for yourself yet?

NM: You can still know what you have to offer, even if you don’t love every part of yourself. Someone can help you discover the parts you’re not ready to love yet. It’s about being willing to let someone love those parts of you. In my own experience, it was hard to have someone like me without having to work for it. 

Trust that someone will love you, and that will help you see yourself differently. I don’t think anyone has to be perfect to enter a relationship. When you’re looking for someone, look for the kind of person who will help you build the qualities you want to love in yourself. Relationships can be a journey of mutual growth and discovery, where both partners support each other in becoming their best selves.

MH: What does success in love or a relationship mean? How do you know you’re in a successful partnership?

NM: Success in a relationship means feeling good, being true to myself, being open to making sacrifices, and working hard to make it last. For me, if my gut doesn’t hurt, it means I’m not trying to fill a void or force something to work just for the sake of it. 

In a successful relationship, I feel completely whole and authentic. It’s about having a partnership where both individuals can grow and thrive together. Success is also about mutual respect, understanding, and being able to communicate openly and honestly. It’s about feeling secure and valued, knowing that both partners are committed to the relationship and willing to put in the effort to make it last.

MH: Have you spent time truly alone to ground into yourself and be ready for a relationship?

NM: I’ve done the alone time and the long relationships, and both are essential. I was single for seven years before my last three-year relationship, with a lot of time to figure things out. I was mostly happy being single. It wasn’t a sad experience—there were a lot of good times. 

Being single allowed me to understand myself better and to grow independently. I had the opportunity to focus on my personal development, pursue my interests, and build a strong sense of self. Now, having been through both experiences, I feel ready for the mirror that a committed relationship provides, where you continue to grow but now with someone else by your side.

MH: How has your approach to dating changed now that you’re in your 40s versus your 20s or 30s?

NM: I don’t linger anymore or waste my time when it’s not going to be a thing. I’m more intentional about who I spend my time with and don’t let my emotions get ahead of me. In the past, I would quickly fall and get excited, but now I recognize red flags earlier and know what’s not going to work for me. I’m more focused on not putting up with things that aren’t right for me. 

I’ve learned to set boundaries and to prioritize my well-being. I understand the importance of compatibility and shared values. I also value my time more and am more discerning about who I invest my energy in. This approach helps me avoid unnecessary heartache and allows me to build healthier, more fulfilling relationships.

If you’re new to Unhinged, catch up on all the dating chats you’ve missed here and follow along at @monicles and @sandiegomag on Instagram to know when a new article drops each week.

Sign-up now for the Unhinged newsletter for exclusive content, Q&As with Nicolle, and subscriber-only meet-ups!

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Looking back, though, money issues never affected us. We made what we made, had the debt we had, and lived comfortably according to those metrics. We went on vacations, ordered takeout often, splurged on fine-dining restaurants, and counted sailing as one of our regular hobbies (hint: it’s not cheap).

And still, money was constantly cited as a reason (among others) why things couldn’t progress.

It’s a common theme. Financial security has been a consistent thread in my relationships and in my conversations, mostly with men, about what someone needs before trading singledom for a committed relationship. 

Greg (not his real name), my friend of about six years, is one of these men.

“There’s a variety of reasons [why I’m not in a relationship], but it all relates back to money. I don’t want to be a burden to any partner,” Greg says. “I have student debt that I always wanted to pay off well before I get married.”

When I talked to him about dating recently, he cited finances as a major reason why, at 38, he’s still not ready to have a girlfriend. 

At the start of 2020, Greg and I briefly dated—we made it about two months before realizing we had no long-term potential. He’s still one of my favorite people, though. He’s thoughtful, funny, and caring, and I sometimes wondered why he’s remained single.

Greg’s been off dating apps for a few years now. “If it happens, it happens,” he says, while also making it clear that he won’t be truly ready until his debt is paid off.

Sounds all too familiar. 

“I want to have the stability, or I want to have this perceived notion of stability through some metrics that I come up with and say, like, ‘Yes, I have the job and the right money where I feel somewhat okay with taking my eyes off of this section of things,’” Greg says.

For as long as I’ve known him, he’s had a stable job and made good money. From the other side of the phone, this feels like an excuse, a faulty plan that may leave him missing out on some really great women. I ask him what “financial stability” means.

His markers, he replies, involve paying off his debt and feeling secure in his job. In my mind, though, things can change in an instant, whether you’re the highest paid person at your company or the lowest. Or, the world could be hit with a global pandemic, which throws everything out of whack.

Nothing is ever guaranteed. Nothing is ever going to be perfect. Isn’t partnership about weathering life’s storms together, finances included? I push him for more as he gets increasingly more uncomfortable with my line of questioning. 

“I think you can still work on [your finances] while with a partner,” I say, and ask where this way of thinking may have stemmed from. 

He shares that it mostly comes from watching his parents. “What I recall is my mom giving [my stepdad] a hard time for not being a decent enough provider,” Greg explains. “I could never be in a relationship with somebody that’s constantly disappointed with what [I] bring to the table financially.”

“Is there any possibility that their experience isn’t going to be yours?” I ask. “Is it a fear because of what you’ve seen, or because you’ve experienced it with a partner?”

“No, I haven’t experienced it… but I won’t allow myself to ever experience it,” Greg says. 

We go back and forth for a little over an hour. He holds steadfast to his view. I remain confident that this metric can’t be something that holds him, or anyone else, back from finding a partner (if that’s what their end goal is).

After a bit of research, I’m not sure if either of us is fully right or wrong. In 2019, a Pew Research study found both men and women earned more and were more financially sound in a committed relationship. Point in my corner.

On the other hand, money was found to be a leading cause of marital conflict in 2024, according to Forbes. And lower income couples have a greater risk of divorce due to money issues. Okay, point back to Greg. 

A 2022 piece from Business Insider says that millennials may delay marriage because of money more than older generations. But financial therapist Megan McCoy suggests that we may actually become wealthier if we get married sooner.

It seems to me that the right person would be open to adjusting their expectations for their partner’s financial situation. Or, for a time, they’d be happy to be the breadwinner until the person with debt can work through it for a more balanced partnership. 

“I am open to it. It’s just not a priority,” Greg says as he questions my argument. “I don’t spend a lot of time thinking about this. But thinking about it now, me not giving myself the opportunity to do this because of a reason that’s obtuse…”

He trails off, and we sit in silence for a few moments.  

“It’s fear, Nicolle, absolute fear,” Greg admits. “I mean, that’s fundamentally it, right? I don’t want to be a let-down.”

There it is.

To put it so plainly is to face the fact that dating from a place of fear simply doesn’t work, no matter what your worries are. Falling in love is one long trust exercise—there’s no guarantee that someone will, for instance, read your column when they say they will, much less treat all the vulnerable parts of you with the gentleness they deserve. 

I think this is worth exploring. Greg isn’t alone in his thinking, and I’m not 100 percent correct in my assessment that finances shouldn’t hold you back from dating. But like Greg mentions, actually taking the time to dissect your reasons for not pursuing relationships may help you figure out what are fear-based hangups and what are real, solid concerns.

If money was the only issue standing between my ex and me, I fully believe we could have made it work. But it wasn’t the real reason we didn’t last, and it won’t be the reason he doesn’t work out with someone else.

And, look, even if a long-term relationship was guaranteed to negatively impact your finances (it isn’t) and to take up more time and require more work than simply being alone (it is), how many people would still seek love? Many, I’d be willing to bet. After all, the rewards of love go far beyond the material. 

And that may be well worth facing your fears.

As for me, I’ve been continuing to go on dates and meet people through my matchmaker. Others have slid into my DMs through this column. Some haven’t worked out, some are upcoming, and one made me laugh the entire evening (but that’s for another time).

If you’re new to Unhinged, catch up on all the dating chats you’ve missed here and follow along at @monicles and @sandiegomag on Instagram to know when a new article drops each week.

Sign-up now for the Unhinged newsletter for exclusive content, Q&As with Nicolle, and subscriber-only meet-ups!

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The post Unhinged, A Dating Series: More Money, Fewer Problems? appeared first on San Diego Magazine.

“I found your article kind of provoking, and I appreciated you writing it the way you did, because I was like, ‘Yeah, that’s exactly how it is,’” Lind says. “Like the thing about false starts and how it can be… It’s so exhausting.”

When I asked him if he’d be up to talking more with me about what dating has looked like for him, he readily agreed. 

Lind is both a professional photographer and a roadie for bands, which means he can be away from home for up to six or eight months at a time. Since the age of 20, he’d been chasing his dreams of becoming a video director (a title he now holds).  

“When I took my foot off the occupational gas pedal [at the age of 34], I had this whole big section of my life that I hadn’t even touched, this romantic side,” says Lind. “I was just so bad at speaking the female language.”

He tells me that, since then, he’s been working on himself through therapy and learning to understand what he wants in a relationship and with a partner. His answer for the latter is pretty simple: someone he can have a good time with, a spark that develops into a deeper connection.

But what struck me during our conversation were the slight contradictions in Lind’s words. He simultaneously declared that he was ready to date and emphasized that he didn’t want to be rushed into anything more serious.

“I don’t want to put any pressure on an early relationship by absolutely saying I want this or that,” Lind says. “Unwarranted pressures on first dates are hard enough. We’re both sweaty and nervous. Let’s chill. Can we have a conversation and see if we vibe and then go from there?” 

By “unwarranted pressures,” he means the big, life-stuff conversations: learning whether your date wants to get married or have a family, talking about how they view a future with their partner. As we chat, he says he feels pretty agnostic about the potential of having children. 

“I need to see the evidence. I need to feel true love before I can feel the idea of bringing a life into this world,” Lind says. “That’s a big responsibility to me, and I don’t take that lightly. I’m not just going to have a kid to have a kid. I would have to have somebody I love and trust in order to bring them into this world.”

He’s weary of these convos when they come up early on. To him, an overeagerness to talk about kids indicates that the other person might be willing to settle just so that they can have a child. I ask him whether that might be a false assumption.

Personally, I know I want children, but that doesn’t mean I’m ready to have a baby with the next willing Y chromosome just because we’re dating. 

“Right. Yeah, certainly. I think that’s very fair,” he replies. 

I’m sure Lind is not alone in his reluctance to discuss serious things early on. But what he sees as relationship-killing expectations might be valid questions that his dates are asking to determine if their hopes for the future align.

Lind, for his part, seems like a sincere guy who has taken steps to know himself better so that he can be a better man for his partner. I do think he’s looking for commitment and will work on being a good communicator once he’s in a relationship. But I can’t help but wonder if the “false starts” he’s experienced are, in part, a result of this subconscious mindset. 

And maybe understanding the way some may approach dates can help him and others put an end to that cycle. 

Being 40 factors into how I show up on dates. I’m much closer to understanding who I am and what I want my life to look like than when I was in my 20s. I’m not as willing to wait around to discuss the things that matter to me anymore, and I imagine that others like me feel the same. After all, the sooner we find our person—the right person, not just anyone—the quicker we are going to be able to achieve those dreams. 

It’s fine that Lind may not want to have those conversations on the first date. But that might mean that someone who is might not be a good fit for him—and who can blame them for wanting answers right away?

What do you think? Does Lind have a point? Does discussing your future desires early on add unnecessary pressure to the first few dates? Or could this way of thinking be hindering singles from moving past the dating stage into long-term relationships?

See you next week!

If you’re new to Unhinged, catch up on all the dating chats you’ve missed here and follow along at @monicles and @sandiegomag on Instagram to know when a new article drops each week.

Sign-up now for the Unhinged newsletter launching this April. Get exclusive content, Q&As with Nicolle, and subscriber-only meet-ups!

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The post Unhinged, A Dating Series: Under Pressure appeared first on San Diego Magazine.

But, after walking her to her car, he turned, grabbed her face, and kissed her. He was cute, so when he asked her out again, she decided to give him the benefit of the doubt. They met up at Fiesta Island with their dogs and chatted during a walk.

“I was asking him questions and he was giving me one-word answers,” says Mackenzie, 37. “So I decided that I was going to not ask him any more questions and just see how much effort he would put in. But he just basically interacted with his own dog.”

After lots of silence, Alex decided to leave. The date lasted 30 minutes.

“I was like, ‘Okay, he obviously feels like this is a bad date. He’s obviously not interested,’” Mackenzie says. “And then he texted me [two hours later] as if that was a normal date. [I’d thought] I was never going to hear from him again.” 

She was confused and understandably over his hot-and-cold approach. Two days later, she said goodbye to all dating apps. I don’t blame her. She’s not alone in feeling that sometimes men lack either the desire or the skills to meaningfully engage, especially when chatting on the apps.

In her column It’s a Pleasure, which focuses on sex, dating, and relationships, author Sophia Benoit offers advice to a reader who hopes to stop having dates with one-sided conversations.

“Not asking questions is, to me, a deal-breaker. Not because it’s impossible for someone to change their behavior, but because you shouldn’t have to walk a fellow adult through basic conversation tips,” she writes.

Finally, someone said it. I’ve struggled with this for years on dating apps, and I never understood it. I thought things might change when I started seeing men in their 40s, but  they have not. And the issue isn’t just anecdotal.

“Research shows that this lack-of-men-asking-questions problem is real, and it’s common, and frankly, it’s embarrassing for them!” Benoit says. “(To all of the 13 men who date women and who do ask questions on dates: This isn’t about you, but please send this article to any man friends you have.)”

So what’s going on here? Turns out there are tons of articles and forums dedicated to this very topic. Women on subreddits like r/Bumble, r/dating_advice, and r/OnlineDating have launched threads asking for an explanation. 

Quartz contributor Elizabeth Weingarten might have one: Social scripts for communication differ by gender, which can lead to confusion and conflict in heterosexual pairings. “In my experience, men who ask questions—the kind that show they’re actually interested in the answers—are rare and wonderful unicorns,” Weingarten writes.

Her sources, including dating experts, psychologists, couples, consultants, and entrepreneurs, confirmed that men have been taught to dominate the conversation as a way to “negotiate for status in the social hierarchy or to preserve independence,” she explains. Women, on the other hand, have learned to use conversations to determine if there’s a connection: “Do we have similar tastes, interests, values?” 

So, sure, sometimes a guy is just not that into you, or he’s distracted by other in-app convos. But it’s just as likely that he’s trying to impress. A man might reason that his date will want to get to know him only after he’s proved that he has the resources or experience to be a great boyfriend. Meanwhile, she’s dying for him to be inquisitive so she can tell if their personalities are even compatible.

In other words: Dudes, skip the peacocking. Relationships will progress faster and farther with genuine conversation. 

“Being curious about your partner helps you know more about them, which leads to the desire to know even more, which creates conversational interactions that lead to enduring intimacy,” writes Dr. Erin Leyba for Psychology Today, drawing from a study published in the Journal of Social and Clinical Psychology.

And that’s intimacy in all forms. Asking questions doesn’t just lead to deep, serious talks. It can also help dates relax and laugh together. You’ll have more fun and, well, better sex.

For what it’s worth, several men replied to the aforementioned Reddit threads pointing out that they’ve faced the same lack of questions from women on apps. Perhaps we’re all fatigued from the difficulties of the modern dating scene (and still getting our social sea legs after Covid). Maybe we could all use a little conversational practice.

Luckily, there are plenty of resources to help us talk to each other. Weingarten finishes her article with five tips for communicating more effectively. You can read them here. 

After all, it seems that the more questions you ask, the more likely you may find yourself enjoying a cold one in front of your potential soulmate.

If you came to the column this week to find out how it’s going with Ryan and Connor, updates are coming! I also worked with my matchmaker to refine my preferences for the kind of man I’d like to meet, so perhaps some more first dates are in my future. As always, happy dating and see you next week!

If you’re new to Unhinged, catch up on all the dating chats you’ve missed here and follow along at @monicles and @sandiegomag on Instagram to know when a new article drops each week.

Sign-up now for the Unhinged newsletter launching this April. Get exclusive content, Q&As with Nicolle, and subscriber-only meet-ups!

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The post Unhinged, A Dating Series: Ask Me Anything appeared first on San Diego Magazine.

We’re four weeks into this series, and I have read every single comment and every single DM. It’s been so cool to see that I’m not alone in not knowing what the hell I’m doing when it comes to romance—and I also want you to know that you are being seen, too; that we are all in this together.

Occasionally, I’ll get some feedback that’s not exactly constructive—or kind—and, for a moment, I wonder why I’m doing this. And then a message like this comes in and reminds me of the reason:

“As a longtime single woman nearing 40, it’s incredibly validating to hear a perspective on dating that is not from the vantage point of: ‘I was single like you once but I found love, and now I hold the SECRET to finding it.’ I think there’s a lot of content out there aimed at single women telling us what we’re doing wrong, so I’m always looking for content that empowers us in our dating process. I’m looking forward to reading the rest of your series!” –Jeannine B., 39

I don’t have all the answers, but that’s the whole point of this series. I’m right there with you, questioning everything and wondering if it’s me, the system, or a little of both. I’m hoping that by being forced to self-reflect each week, I (we?) can begin to understand how to date in a way that feels intentional, fun, and rewarding.

Besides, there are plenty of other incredible voices, experts, and content creators in this space with in-depth knowledge and years of research that are giving great advice—people like matchmaker and SD local Sophy Singer, who has spent 14 years finding matches for singles.

For this week’s installment of Unhinged, I tapped Singer to answer some looming questions I had regarding today’s dating culture. Here’s what she had to say: 

Are there any questions that can help people get a deeper sense of someone other than the typical first date lists? 

“What are your top values? What’s most important to you in life?”

I think a really cool question to ask—because I ask this when I screen people for matches—is, I ask them about their past relationship. “What was your takeaway from that relationship? What did you learn?” You want to know how self-aware they are. Are they pointing the finger toward the other person only?

Is there anything you’d steer clear of as topics for a first date? Like if someone’s a single parent, or if religion is very important to them, when should you talk about these things? 

If you asked me [two-and-a-half] years ago, I would have said don’t talk about politics. Don’t talk about religion. Don’t talk about sensitive topics.

Not anymore. Talking about sensitive family topics—I didn’t welcome that because I used to be very ashamed of my own family history. My parents divorced and my father went to jail. And I was like, “I don’t want somebody to ask me that, and I don’t want to ask them. I don’t want to get uncomfortable. I want things to be light and fun.” And of course they can be light and fun. That doesn’t mean you can’t have fun on a first date. 

Let’s say, for example, you’re on a date and religion is important, right? You bring it out and talk about it and you can say, “Hey, the reason why I have this curiosity is because I have this value around this.” [Or] you can just say, “Actually, I want to talk about this stuff because I have such a curiosity on where you fall here and what value this is for you.”

But, also, be aware that trauma bonding is not a great idea off the bat. I would say it’d be good to have self-awareness. [You can say], “You know, I feel like this is a little edgy and maybe going a little too deep, so please let me know if you are open to me asking and please know that you definitely don’t have to answer.” You can always just create a little bit of softness around that.

After a first date, how can you tell when your gut is saying “This person isn’t the right match for you,” or whether past fears, traumas, attachment styles, or experiences are affecting your mindset?

Well, first thing is, how aware are you of yourself and the parts of you that pop up? The fears and blocks. 

If you’re more self-aware, you have a better idea [of how to say,] “Oh, I’m having this reaction. Oh, this must be based on my past. I’m reacting because of this.” Or, “Oh, this is something I don’t like about myself. And that’s why I’m annoyed by this other person. Maybe I need to work on that.”

[Going on a] second date should always be the default, unless it’s obvious—like if they show up and they’re just super off-putting. But maybe they weren’t opening up. Maybe they’re nervous […] because sometimes people really are nervous on a first date. So I think a second date should be the default [to determine if you’re a match]. 

What do you do when the other person isn’t being intentional about dating you? For example, some have said things like, “Oh, I just don’t plan dates,” and only ask to hang out last-minute when they have nothing else going on.

I think it’s frustrating because it makes us feel like seeing you and spending time with you and the relationship is not really enough of a priority to plan ahead. Sometimes it indicates, for me personally, less of a respect of my time and my energy. That’s not necessarily their intention or where they’re coming from, but that’s how it makes us feel. 

If you want to depend on other people to determine your experience, great. You could sit around and just decide that that’s what dating is these days. Some people think that’s easier. I think it’s harder. 

So [have a] conversation: “I [appreciate] making plans ahead of time […] with somebody that I’m getting to know and making sure that that happens in a little bit more of an intentional way. I don’t have to have every single date planned ahead of time, but I do value having that be a part of dating somebody.” 

Are we going to just dismiss [someone] and let this potential connection die immediately, or are we going to reveal our needs and give the other person an opportunity to step up to meet you there? Because if we don’t let them know where you need to be met, how can someone have the chance to do that? They can’t read your mind, and everybody comes to dating from different places.

If you’re new here, catch up on all the dating chats you’ve missed here and follow along at @monicles and @sandiegomag on Instagram to know when a new article drops each Friday. Have questions you want answered in the column? Email Nicolle at [email protected] with topics you’d like to see covered.

Sign-up now for the Unhinged newsletter launching this April. Get exclusive content, Q&As with Nicolle, and subscriber-only meet-ups!

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The post Unhinged, A Dating Series: Better First Dates appeared first on San Diego Magazine.

“What I’m hearing is that you don’t like to be the one answering questions because you don’t feel like you have much to offer,” says a stranger sitting in front of me, five minutes after I meet him.

I start to sweat. This happens a lot when I get nervous, and not in a charming way. It’s the kind that lingers on your upper lip as you talk so you’re continually wiping your face. 

With no plans for Valentine’s Day, I’d decided to take part in a Feb. 14 singles event hosted by matchmaker Sophy Singer of Sophy Love. As a group, we’ve just finished an hour-long workout, but this is the first moment where my sweat feels embarrassing. 

I’m sitting in a large circle. It feels as though neon signs blink overhead, calling out my insecurities, as I scan the room of 25 other singles. We begin the second half of the mixer, starting with a meditation before discussing “authentic relating,” a concept that author Ryel Kestano laid out in his book Authentic Relating: A Guide to Rich, Meaningful, Nourishing Relationships. 

As we meditate, I question why I’m here, who I could ever meet in this environment. Is finding a partner just not for me? Is everyone else as uncomfortable as I am?

Being a little uncomfortable is kind of the point, though. Authentic relating is designed to slice through the shallow pleasantries of the typical first date. “When you practice authentic relating, you are bringing your whole self into the relationship,” Singer says. “You’re not strategizing; you’re not playing games; you’re not changing yourself to be some version that you think the other person is going to like better than the real. And being seen and heard is healing.”

Kestano defines three levels of conversation: informational (pure facts), personal (feelings about facts), and relational. 

“[The relational level] is a conversation where you are revealing your experience and what it feels like to be in this moment with the other person. It is always new,” Singer explains. “It is unscripted. This moment that we are having here has literally never happened before.”

According to Singer, level three is the game-changing key to connecting authentically with others. She asks us to share with each other what is “alive” for us in this moment. In less woo-woo terms: How are you actually feeling as you’re being asked to get to know this person?

As we follow Singer’s prompts, my conversation partner zeroes in on the fact that I tend to push attention off of myself because I don’t enjoy feeling vulnerable with strangers. (Truthfully, this column is not easy to write, at all.)

It’s a far cry from the “What do you do?” convos I usually have with acquaintances. In this setting, I couldn’t feign perfection and hide the parts of me that feel complicated or weak. But neither could he.

As we spoke, I learned that he had never participated in any type of dating meet-up or event like this and that it was overwhelming for him—so much so that during a mid-session break, he quietly slipped out and went home. Nevertheless, our mutual willingness to analyze our reactions and interactions humanized him. I found myself caring about him more than I would have had we just prattled about our favorite hobbies. 

This is what seems to be missing in dating right now. Frustrated and fed up by endless failed dates and used to the split-second decision-making of swiping on apps, we might find it difficult to muster the energy to really connect with someone new, at least until we’ve assessed whether they’re worth the effort. 

But maybe that’s the problem. What if we approached every date as a chance to engage with an interesting new person, whether or not it leads to a relationship? Every stranger has a story to tell. “We think that people connect to the glossy version of ourselves,” Singer says. “ But actually, where most connection takes place is with the messiest parts of our human experience.” 

And, if we buy into Kestano’s words, being willing to get deep right away can help foster relationships built on honesty, integrity, trust, and wholeness.

The singles event wasn’t what I had expected, and it wasn’t always easy to release my ego and follow Singer’s suggestions. But I’m glad I went. The thing is, though, I’m nervous to share this post this week, because it all feels so obvious. 

Yet, from what I’ve seen—and read in the flood of DMs I’ve received since starting this series—we’re not actually putting these ideas into practice. Could our perspective on dating change if we started seeing one-off dates as a good thing—an opportunity to learn something new about others and ourselves?

After all, I didn’t meet anyone that night, but I did use some of these methods on my first date with Connor (not his real name) this past Monday. He asked me out again (more on this later). Maybe he was attracted to my mess.

As always, thanks for following along. See you next Friday!

Follow along for all the fun and updates at @monicles and @sandiegomag.

Sign-up now for the Unhinged newsletter launching this April. Get exclusive content, Q&As with Nicolle, and subscriber-only meet-ups!

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The post Unhinged, A Dating Series: A Lesson in Ego appeared first on San Diego Magazine.

He told me he wasn’t ready for a relationship pretty quickly after we started talking. I, of course, ignored it. He just needed to get to know me. 

Let’s call him John. As we grew closer, our relationship became intoxicating. We had undeniable chemistry, and he soon became a drug I couldn’t give up. I was hooked. We spent every day together, talked about the future, and called each other best friends.

But John wasn’t ready to commit, he said—which led to arguments and, eventually, break-ups. Each time, I went through intense feelings of withdrawal: depression, loneliness, low self-esteem. But I continued to run back to him, believing still that he’d change his mind. 

During off times, I tried dating, but I was always waiting for the pendulum to swing back with John. I didn’t realize it then, but I shouldn’t have been trying to meet anyone new. After this column went live, a friend reminded me that her guy friend had once tried to take me out. 

I got a migraine the day of our plans and had to cancel. He then left on a two-week trip, and neither of us followed up when he returned. My date had assumed I’d reschedule since I canceled. I don’t remember exactly what I was thinking during that time, but I do know that I didn’t have space in my world for anyone but John. 

And this probably left a good man wondering what had happened.

Admittedly, back then, I was part of the current dating problem. Some of us jump on the apps or into relationships before we’re actually ready, before we’ve fully wrestled with the loss of someone we once loved. This creates an endless loop of false hopes.

For me, the feelings I had for John felt like an addiction—not something you can work through overnight, or even a few weeks. Mourning my hopes of a relationship took a lot longer than I thought it would. But from stories I’ve heard, and ones I’ve been a part of, I’m not alone.

“Most people are delusional thinking that they’re ready; I was [once] one of them. That’s why I can say it with so much [confidence],” says Sabrina Zohar, an SD local and host of the Do the Work podcast, which focuses on dating, anxiety, and healing. “I think that’s why we find ourselves in those loops.” 

She’s right. Many of us have been on either the receiving or giving end of a “not ready” conversation. I came across a TikTok recently from a creator who said, “If you can heal from a breakup without using another person to fill that void, you’re actually very strong.” Whew. Heard.

In trying to date while still hung up on John, I likely unintentionally hurt people or missed out on really great connections. After all, what we look for when we’re really ready to commit is likely different from the more superficial markers of a great rebound. 

“You could make it work with a lot more people than you think,” Zohar says. She shares that studies have shown that the true markers that are needed to be compatible with someone are not the must-haves we seek when we’re rushing to fill the space our partners left behind. 

“Are they hot?” “Do they have all the same interests as me?” “Do they meet my financial requirements?” These questions may be helpful for finding someone to get along with, but in the long run, they don’t measure whether a partner can stand by your side in the good and bad, in sickness and in health.

Instead, Zohar suggests asking yourself, “Do you have similar goals, ethos, morals, ethics, are they a good person? We are so conditioned to think, ‘I need this,’ or ‘I need that.’ But an actual healthy and secure relationship is none of that.”

So, the first step to making lasting connections is looking inward and becoming more self-aware. Maybe we can stop the loop.

We also have to be careful not to romanticize the future with someone before we have a real sense of whether we’re willing to be in another relationship. That false hope can be just as damaging. 

And when someone is honest with you about what they’re looking for or aren’t ready for, believe them. You won’t change their mind. I learned this the hard way. The time I spent trying to convince John that I was worthy…I mean, what would my life look like had I given myself or others that energy instead?

This is the first time since him, though, that finding someone great has felt like a real possibility—which is how I found myself in a sweaty meditation circle with 26 other singles in Solana Beach on Valentine’s Day.

But that’s a story for next week. 

As for my matchmaker, she found my first date. So stay tuned! And thanks for following along on this adventure. If you see me walking around at our Taste of South Bay event this weekend, come say hi, share your dating stories, or ask me out—whatever floats your boat.

Follow along for all the fun and updates at @monicles and @sandiegomag.

Sign-up now for the Unhinged newsletter launching this April. Get exclusive content, Q&As with Nicolle, and subscriber-only meet-ups!

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The post Unhinged, A Dating Series: It’s Me, Hi, I’m the Problem appeared first on San Diego Magazine.

Last year, WalletHub named San Diego the ninth best city in the US for singles wanting to date. But if my dating apps and convos with other local singles are any indication of how true that is, I call BS. Sure, there are plenty of people open to dating, but finding commitment in a city full of Peter Pans is a different story.

I’ve lived in San Diego for 15 years and have dated in this town in my 20s, 30s, and now 40s. I’ve spent weeks chatting with a potential partner only to learn later that they aren’t ready for a relationship (even though their profile said otherwise). I’ve even had a guy leave my side to pick up food for a BBQ, then text me from the road that he’s breaking up with me. 

I recently read a quote from Glynnis Macnicol, author of No One Tells You This—her debut memoir on women and singleness—that rang true. “Culturally there is a lot of messaging out there that after the age of 40, if you have not acquired a partner or child, you are sort of in a no man’s land of invisibility,” she told Refinery 29.

Oof. I feel this.

Being single in your late 30s and 40s (not by choice), feels invisible—at least as a woman. You’re unseen, you’re in the way. No one really knows what to do with you in the dating world. You’re out of the PB nightlife scene and past the cut-off for young professional meet-up groups. Your married friends only have married friends. And dating apps just aren’t working anymore.

Then you have the US Census Bureau telling us that, currently, 57 percent of single adults aren’t interested in a relationship or casual dating. Great. Perfect. And according to a recent PEW research study, “A quarter of 40-year-old Americans have never been married, more than in any other time since data has been collected.” 

Have we all just given up? Or has the culture shifted so far to one side that we’re all messier, more discontent, and unsure of how to make real connections nowadays?

I’d like some answers, or at least, some guidance on how single people are supposed to navigate a world filled with swipes, ghosting, and grown-ass adults saying they aren’t ready to commit. 

My last relationship lasted three years, but there were so many ups and downs that I’m still working through some lingering whiplash. I inevitably redownloaded the dreaded apps. Hinge was my go-to. After a year, I deleted it one night in a fit of frustration. 

So, over the next few months, I’ll be ditching the apps (getting un-Hinge-d, if you will), diving back into the wild world of dating, and sharing my experiences right here for all. I’m hoping that by getting vulnerable, while digging into San Diego’s dating scene, those who also feel unseen can start to realize they’re not alone. Together, maybe we can learn how to better find love in 2024. I’m genuinely hoping to meet someone special.

I’ll be documenting my personal dating experiences while working with local matchmaker and relationship coach Sophy Singer, dissecting dates and conversations, talking with experts in the field, unearthing current research on dating and mental health, and recounting the stories of other singles in San Diego so that we can figure this out together.

Up first: Tonight’s Valentine’s Day workout and mixer with F45 and Sophy Love. A little flirting, a little sweat, and a healthy amount of awkwardness—honestly, it sounds just like my first time.

Follow along for all the fun and updates at @monicles and @sandiegomag.

Sign-up now for the Unhinged newsletter launching this April. Get exclusive content, Q&As with Nicolle, and subscriber-only meet-ups!

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The post Unhinged, A Dating Series: Seeking Answers appeared first on San Diego Magazine.