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Unhinged, A Dating Series: Assumed and True Dealbreakers

Exploring the "whys" behind your boundaries can help decide the difference between a red flag and a worthy relationship challenge
Dating advice column Unhinged by San Diego Magazine covering dating red flags vs dealbreakers in relationships

I wasn’t sure I’d ever feel butterflies for someone again. When my long-term relationship ended last year, I couldn’t have imagined that in several months’ time I’d be trading messages and stories, laughing over new inside jokes and finding so many points of connection with someone like Robin (not her real name).

I met Robin through Hinge one night while sipping wine with friends and talking about the kind of partner I’m looking for. When we connected, she started chatting with me immediately. It was a relief to not have to guess at her level of interest; she led with authenticity and vulnerability. With her, things seem a little brighter. I’m smiling a lot more. I feel like maybe the future will be much better than I even hoped for. 

But at the same time, I’m also terrified of screwing it up. I constantly have that “other shoe” feeling, like I’ll make one wrong move and it’ll all be over. 

In the early days of dating someone, when you still don’t know them that well, it’s impossible to know what they’re thinking about you or who they’ll turn out to be. I’m scared of ending up in the same type of situation I was in before: stifled, shut out, abandoning my own needs to try to fix something that was not salvageable or serving me.

Unhinged, A Dating Series with Nicolle Monico

I’m forcing myself to gut check, take a step back, vet Robin against the values I’ve instilled in myself since my breakup. What are my dealbreakers? Will I be able to enforce my own boundaries knowing that I’m so excited to see where this goes? It’s hard to temper excitement with guardrails, especially when you’re seeing someone through rose-colored glasses.

One benefit of leaving a long-term relationship is that you come away with absolute clarity about what you were missing while you were in that partnership. Hindsight looks clear as day, and you tell yourself, “I’m never going to put up with that again.” You walk through your single life with focused assurance you will never repeat the same mistakes.

And then inevitably, you meet someone new, and they bring a fresh set of variables, quirks, and baggage. You’re on the lookout for old ghosts: the poltergeist of chaotic living standards, the apparition of abandonment issues. But how should you contend with new information that may not look like the former foe you know so well?

It’s prompting me to get clear with what my dealbreakers actually are and which ones may no longer apply. What’s the difference between a true red flag—something that goes counter to my needs or values—and a trigger from my past that can be navigated with the right person?

For instance, I’ve often thought that I would never date someone who is a huge sports fan. What I’m realizing is that I don’t vibe well with people who are hyper-competitive, and I’m turned off by frivolous spending habits (like constantly buying merch, betting on sports, or attending expensive games super regularly). The subject matter of sports is beside the point—it’s the actions behind it that I’m focusing on. If my core values aren’t being violated, I find I’m much more willing to cheer for the home team.

Similarly, I have told myself that I wouldn’t again get involved with someone whose job took them away from home often (Robin’s does, as did my ex’s). But I’ve realized the issue was a lack of communication, planning, and reassurance—and the fact that my own world wasn’t as independent and developed as it needed to be for me to feel grounded when she wasn’t around. I’m realizing that I can sustain a situation like that much better if I feel prioritized by my partner when she is home and free to prioritize myself when she’s not, knowing she will check in and communicate with me in a way that makes me feel safe, not abandoned.

With all of this reflection, I can’t help running into a terrifying thought: What if what I bring is a dealbreaker for her? What if my imperfect life is just too much, and she heads for the hills? My new flame has a lot of rules for herself—she holds herself to an incredibly high standard in terms of personal growth, organization, and work ethic. I’m impressed… and intimidated.

San Diego restaurant Nolita Hall featuring affordable date night deals including their "Girl Dinner" special

I’m doing my best to rely on the work I’ve done on myself in the in-between. To not have the impulse to change myself in order to impress her, but to lead with my best self. My true self. This isn’t about trusting the other person to protect me but trusting myself to be resilient if we aren’t right for each other in the end. I’m motivated to get clarity about her dealbreakers, too. Is there anything there that is truly integral to who I am as a person, or is there a behavioral aspect here that I’m comfortable changing? I do think it’s fair to make accommodations for someone without it fundamentally changing who I am. 

For example, I am more relaxed about home organization than she is. I’m not messy, but I will also leave the odd glass hanging around the sink or keep my hair products out if I’m in a rush. We have discussed our preferences, and she has shared that it’s more a tenant she holds for herself than for a partner. I don’t feel pressured to change how I am normally. At the same time, I’m inclined to do a little extra around the house if it means creating a space she feels comfortable in.

It’s early days, and we still have so much to discover. For now, I’ll be keeping these considerations in mind as I enjoy all the fun things, too.

Tell me, what are your dealbreakers? How early have you left a relationship because of one (or how late)? Have you ever had someone abandon you because you set a boundary or because you had something integral to you they couldn’t get past? I’m so curious.


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

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