I'm Anxious About Getting My Heart Broken Over & Over Again

Q: I am the stalwart single person in my group of friends. I pretty regularly go out with people I either meet on the apps or in person, but nothing ever seems to progress past a few dates. Sometimes I realize that I’m just not that interested in the other person and sometimes it’s the other way around, of course. But when I am interested in someone, I’ll often fluctuate between feeling pretty confident and feeling really anxious that I’m just going to get my heart broken again.

Part of this, I realize, is me getting my hopes up too quickly. A lot of dating, especially in the large city where I live, starts off pretty casually, which means I often feel like I’m leaning too far over my skis when I start to like someone after a couple of dates. In the past, I had trouble believing those romantic feelings could ever be mutual, but some good therapy has helped me become a lot more confident in the past couple of years.

Yet that anxiety always turns up again when things don’t work out, and when I meet someone I like, I feel like I’m just waiting for them to call it off. When they do, I’m caught feeling heartbroken over something that never began. And I’m torn; I know that things would be easier if I just chilled out and tried not to care if these things worked out or not, but sometimes I do genuinely care, and I feel like I will never really connect with someone if I just pretend not to care all the time. Part of me wonders if that anxiety itself is the reason these things don’t work out.

I know that you have to be willing to feel the difficult stuff if you want to feel the good stuff. But I’m getting really tired of this pattern repeating itself over and over, and my friends don’t understand what it’s like. Sometimes they try to offer explanations for why things worked out a certain way, but they never really seem to get that I’m feeling sad. Meanwhile, I keep putting myself out there, but it’s getting harder to keep believing that something will eventually work out.

Any advice on how to not get ahead of myself without missing a chance at connection? And maybe how to get the kind of support I need from my non-single friends?

A: When I first started dating my boyfriend, I was freaaaaaking out. I mean, just absolutely losing my sh*t. Of course, when around him, I kept all of that shoved deep down inside (until it would occasionally explode with disastrous results). In my journal, in random Google docs I’d open at my day job, and to my friends, I would spill out all my fears and concerns. I simply didn’t know what I was doing; I’d never dated someone I actually liked before. In fact, I’d only dated one other person at all before. I was a knot of anxieties. As it turned out, I didn’t need to worry.

The problem of course, is that when you first start seeing someone, you don’t know how it’ll end. You don’t know if this thing you’re putting effort and hopes and weird sex positions into is going to pay off or shipwreck your life for four to seven months. You have no idea if the small, weird feeling you get sometimes is boredom or nerves or true, glaring incompatibility. It’s very alluring, therefore, for your brain to try to test-run every single possible outcome before it happens, vacillating wildly between images of doom (which urge detachment) or fantasies of long term bliss (which urge premature devotion).

I couldn’t figure out if my boyfriend was terrible for me and I was being a foolish little cabbagehead or if we were on the right track. I wasn’t so much worried about heartbreak but I was fixated on Making the Right Decision, and making it as soon as possible. God forbid I dither when deciding about a romantic partner.

I got so frustrated that I came up with a mantra that I wrote down and repeated ad nauseam: “Let this be all that it is.” Look, the phrase is embarrassing and not all that perspicuous. But it reminded me not to cut off something good simply because I was scared. I knew my habits tended towards leaving people or backing out of things, and I wanted to let this actually unfold. I also wanted to enjoy my time dating him even if it came to an end sooner than I wanted. If it was going to end, and this was all it was going to be, OK. Let it be. (I think I somewhat succeeded. I mean, we’ve been dating for seven and a half years now.)

Now, having a little mantra isn’t going to remove all doubt. But if you find something that works for you, it might be a good touchstone for the moments when you’re getting ahead of yourself. As you get to know someone new, focus on how you’re actually feeling in the moment now. Are you enjoying your time together? Do you dread hanging out? Are you dissatisfied in bed? Are you excited for them to meet your friends? Let these feelings guide what you do next. You don’t have to plan the whole relationship out in your notebook M.A.S.H.-style, but if things are going well, just keep trucking along.

It’s fine to have feelings — preferred, actually! You can’t simply ignore the painful parts of dating.

Trust that if things are bad in the future, you will know to leave. If things are good in the future, you will know to stay. You can’t make someone feel the way you do, of course — the connection can be wonderful for you even if the other person doesn’t feel it. Chemistry can be tough like that. But your job isn’t to sniff out the perfect relationship as soon as possible and discard everything else even faster. Your job is to show up and be present.

You say things would be easier for you if you “chilled out,” but please notice that that is not my recommendation. Nobody wins an award at the end of their life for being chill. It’s fine to have feelings — preferred, actually! You can’t simply ignore the painful parts of dating. The goal isn’t being unaffected. Instead, try to experience the hard parts when they come rather than trying to anticipate and outsmart them.

Now, how to bring heartbreak and other dating woes to your friends: I recommend that you think about the kind of responses you’re looking for. I know you say support, but what does that look like for you? You can say outright, “Hey, I’m just looking to complain for a bit, and I don’t need advice but…” Or if you do want some, “What would you do if you were me?” Or if you have a really honest, close friend and this fits with your vibe, “I’m really struggling with this pattern. Is there something you think I could work on that might help?” Ultimately, the reason you’re single is most likely because you haven’t met the right person yet. It’s not some hidden deficiency. But sometimes, we can come off in ways we don’t realize. Our intentions get lost in translation. So it might be worth asking the question.

You might also put some effort into finding another single friend or two to commiserate and celebrate with. I don’t think that people’s ability to be a good friend changes wildly depending on their relationship status, but there is sometimes an acute understanding gap between single folks and partnered people. You might find it helpful to connect with people who are going through something similar.

Dating can suck. You’re allowed to complain. It’s very, very human to get ahead of yourself, both in wanting to fantasize about the future and to prevent potential pain. Try to slow down and enjoy whatever stage you’re in. (OK, maybe not heartbreak. But even that can push you into building resiliency and empathy.) You do not have to stop being anxious about the future entirely — that’s probably not possible, so cut yourself some slack — but remember that change always comes, no matter what. Can you look toward the future with curiosity instead? It’s fine to be nervous, but trust your gut. You’ll know what to do.

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