You Need Help: So Your First Girlfriend Broke Your Heart — Now What?

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Q: I was broken up with three years ago by my first girlfriend (it was bad. A bad relationship but also a shattered heart at the end). And now I’ve kind of met someone new but I’m terrified of going out with her because I don’t want to hurt again (classic) and I’m currently not 100% sure about my feelings for her, so I don’t want to hurt her either.

Also though I’m still kind of thinking about the last girlfriend. I’m pretty sure I’m over her, but I still occasionally stalk her on social media and even now thinking about dating the new girl, I can’t help but think of the old gf seeing pictures of us and maybe being jealous. I mean how delusional is that.

I just don’t know what to do. I know you have to date people to end up with someone (if that’s the goal, which in my case, it is) and I know there’s something to be said for just having fun and dating people even if it doesn’t work out but I feel like I need to protect my heart in the process, but that also seems impossible.

Anyway, that is my story. Any advice?

Hello dear friend.

There’s so much to chat about here, and this is one of those questions where there’s not a right answer. This is one of those questions where there isn’t even one question. So I’ll tell you what — right now, I’m in my pajamas and I’ve got a nice glass of wine. It’s 11:11 pm (make a wish!). My fiancée is asleep already and I’m still on the couch with my computer, writing to you. What I’m going to do is pretend that I know who you are, that you’ve stopped by my apartment right about this time. I want you to pretend, as I am doing, that I’ve lead you to the grey armchair in my living room, poured you a glass of Malbec or tea or water — maybe I’ll even have mixed you a drink from my bar. And we’re just going to shoot the shit about this one. Because there is no prescription for what you’re going through right now, not even more cowbell.

First, I want you to know that everything is going to be totally okay.

Now to tackle your first paragraph — I see two things going on here. You want to protect your heart and you want to protect her heart. This is good. You’re not emotionally reckless. But I want to explore the notion of emotional safety. Have you heard of the sex education community’s push to talk about safer sex instead of safe sex? I know, I know, you didn’t ask about sex. But that’s usually the kind of question I answer, so just take my hand and go with me here. The reason this push exists is because there’s no such thing as sex thats totally safe — hell, once I burned my hand on a massage candle. Once a cat jumped on my back during sex and raked his claws from my shoulders to my hips. Even when all practical measures have been taken, there’s still a chance that something will happen to you that you didn’t plan for.

I bring this up only because I think we need to talk about safer dating. Safe dating is a myth. I was going to type, “anytime there are two people involved, there is potential to get hurt.” But I actually want to take it a step further than that: any time a person exists anywhere on the planet, and they don’t even have to be taking actions at the time, there is potential for that person to be hurt. Kinda sucks, right? Except it doesn’t; accepting the reality that romance, dating and emotional life is never 100% safe is liberating. It normalizes yucky feelings and missteps and false starts. It provides a context in which we experience heartbreak without breaking our souls. Heartbreak is common, and you aren’t alone here. Chances are the girl you’re talking about has her own experiences with heartbreak as well.

Now I also hear you’re not sure about your feelings for her, but alas friend. The way you figure out your feelings for a person is by spending time with them. Much of the time, that involves dating. So how can we synthesize the concept of safer dating into your situation, here? Well, actually that’s not something I can definitively answer for you because you didn’t tell me what was bad about your last relationship and your last breakup. But let’s engineer it backwards — what sucked last time? Was there a specific action or boundary that could have prevented it from sucking, or made it suck less? Sit down with a journal, and make a list. Go ahead, I’ll leave you to do that in my grey armchair in my living room. I’ll even pour you another glass of… what was it you were having again?

Are you finished with that? Cool — maybe not on the first date, because usually that’s reserved for things like, “what’s your favorite color?” and “Do you know all the lyrics on the Wicked soundtrack?” But maybe when you get around to a second date (if there is one), or a third, you mention the specific things you’re looking for out of dating. For example, if one of the things that sucked last time was you moved too quickly before you really got to know your ex-girlfriend, be really clear how you want dating to proceed this time. You might say, “last time I jumped in with both feet and that was an experience I needed to have. This time, though, I think it might be better for all parties concerned if we take things slower and I get to know you one step at a time.”

Now the secret here — whatever these boundaries are, however you want dating to proceed — if the person you’re looking to date doesn’t have the same ideas, you might want to question continuing the dating process. That’s what safer dating is all about, right?

There was some other stuff you mentioned that I’d love to chat about. You mention you’re still kinda Googling your ex, and that there’s an aspect of moving on that’s performative and done for the benefit of your ex’s imagined jealousy. You recognize that these behaviors and feelings aren’t emotionally productive for you. So I’m going to offer up some advice that I feel like some people will disagree with: just stop doing that. I actually think not looking your ex up on social media, and I mean ceasing the action, will eventually stop the resulting feelings. We fall into patterns of behavior, and the way we act is directly linked to the way we think and feel about ourselves and the world — think about the common advice to build a habit of out-loud positive self-talk. Ending the pattern behavior can go a long way to ending the feeling — but what if the two are connected in a vicious cycle of terrible things and thinking? Every time you get the urge to look up your ex-girlfriend, or to alter your behavior based on her imagined reaction, as yourself one simple question: “do I really care?” And no matter what you actually think or feel, answer yourself, “no.” And rationalize that. Come up with why you don’t care.

Here are some example reasons why you absolutely do not care what your ex is doing right now, or what she thinks of you:

• Because her thoughts and feelings have no impact on your day-to-day existence.
• Because you’re too busy with [insert literally anything here] to devote any space in your life to something as unproductive as caring. (A simpler way of stating this: You’ve run out of fucks to give.)
• Because you didn’t trust her judgement of you at the end of our relationship and you still don’t trust it now.
• Because exploring your own thoughts and feelings is a better use of your time than imagining hers.

I could keep going, because there are a bajillion reasons why you actually don’t care. Now if you were just a few weeks out of this break up, I probably wouldn’t give this same advice; everyone needs a wallow period, as evidenced by season one, episode seventeen of the Gilmore Girls. But you’re three years out. Your wallow period is long over. No matter what, you do not actually care! Here’s where I pour you a third glass of whatever it is you’re having and we accidentally wake my fiancée up because we’re screaming “WE DON’T ACTUALLY CARE” back and forth to each other in my living room.

All this is to say that I think you’ve got this. I think you should move forward and have at least a first date — ask her if she knows what happens in season one, episode seventeen of the Gilmore Girls. And if she answers that question correctly, well then. On your second date, be crystal clear about what safer dating means to you. Don’t make compromises that compromise your emotional safety, and have fun! You can do it. I know you can.