How I Keep From Being Cynical When Dating Totally Sucks

Photographed by Rachel Cabitt.
I used to never understand people who would wax poetic about the beginnings of relationships. They’d go on about how much they loved the newness of everything — the first kiss, the first time they had sex, the first time they realised their partner hated the same things they hate. People talk about the honeymoon phase in relationships all the damn time. But the first month for me rarely feels like a honeymoon, which I assume is just a suspended state of holiday sex. No, the beginning of a relationship for me always feels like waiting for the other shoe to drop.
I’ve been dating since I was 17, so for the better part of a decade. And I’ve only spent about three of those years in “serious” relationships, which I define as “we call each other boyfriend and girlfriend, you’ve met my parents, and we’ve gotten into at least two huge fights that didn’t end in a breakup.” The other seven-ish have been spent single, bobbing between different levels of non-relationships. In fact, my mother and I calculated and decided that, in 2015, I’d gone on something like 70 dates. That is a huge number of hopeful situations that have turned into absolutely nothing.
So it’s natural that someone like me can become cynical and untrusting when it comes to relationships. If the majority of your experience has been “failure”, then how do you continue to remain hopeful that someday you will meet a person who will want to stick around — and who you will actually want to stick around, too?
I don’t think I realised how bleak my outlook was until a few weeks into my last relationship. I found myself assuming the worst outcome of every situation we’d find ourselves in. Two hours before our third date, he mentioned that a client of his messed up the time of their meeting, and that she thought it was an hour later, which would have run into our dinner reservations. I figured he’d cancel on me and, since I was travelling the following week, that third date would never happen and this thing would just fizzle and why are you even doing this anymore, Maria?! That was typically how these things went for me.
This time, though, he told his client he’d see her another time and met me for dinner instead. So I decided to just let things roll for a bit — and not project on him all of my feelings of hopelessness from past relationships, and just kind of enjoy the ride. This served me well throughout our relationship. But then, after a week of things slowly deteriorating, he slept with someone else. This was a betrayal to me, because even though he wasn’t my official boyfriend, we’d decided to be sexually exclusive. I ended things once he told me.

The beginning of a relationship for me always feels like waiting for the other shoe to drop.

I felt like total shit. Not only did I have yet another failure to add to my list, but I’d now had my first experience of being cheated on, which tossed distrust on top of the cynicism that was rearing its ugly head again. I was settling into Negative Town, and I realised it on the first date I went on post-breakup. The guy was terrible and since I was feeling shitty, I was probably the most negative I’ve ever been on a date. I lamented how bad the dating scene in New York was, talked about my breakup, and actually told the guy that “men don’t know what the fuck they want.” We parted ways after one drink.
Negativity is an easy trap to fall into, says Rachel Sussman, psychotherapist and author of The Breakup Bible. “If you’re going to date, you’ve got to stay optimistic and go into each date with an open mind,” she says. “If you can’t do that, you might have to give yourself some time to heal.” So that’s what I’ve been trying to do. I haven’t completely shut myself off to dating, but I am taking a lot more time to try to get a sense of a person before I take the time to meet them IRL. I’ve also been taking a lot more “me time” to remind myself that I’m totally okay on my own, and that failed relationships don’t mean that I myself am a failure.
One of the most important points to remember, though, is that my former partner’s cheating had absolutely nothing to do with me. “If you do your work to heal, you’ll understand that the issue was with that person and that relationship,” Sussman says. “That should be your remedy. You can’t go into every relationship thinking that the next person is going to cheat on you.” Just like I can’t project all of the past failed relationships onto my next date, I can’t project that cheating energy, either.
The cynicism still bubbles up from time to time, but I try to remind myself that most people weren’t put on this earth just to fuck with me. Sometimes things just don’t work out, whether it’s because of timing, distance, or the fact that not everyone is going to like everyone else. And, given the number of people I’ve dated and will probably date in the future, there’s likely a greater chance of things not working out on any given first date than there is of that person being my soulmate — and that’s totally fine. Not everyone can be The One. So I’m trying to have more fun with the process and stop taking things so seriously. “If you go in with that attitude, the date will never be a total bust,” Sussman says. If anything, it will be a hilarious story to share with your friends over a cocktail.

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