Love Letters

How long can we just flirt?

Q. I just got out of a two-year relationship with my ex-boyfriend, and I devoted a lot of my time to the relationship. I was too blinded by love to realize that all he cared about was sex and himself. I realized that after we broke up, unfortunately. It’s been almost three months since we broke up and I’m slightly over it now. If I think about my ex too much, I break down (that only happens if I’m left alone, which is kind of rare).

Recently, I became friends with this woman (I’m bisexual), and we’ve been flirting harmlessly — like friendly flirting. I’m scared to pursue it because I could fall in love or maybe hurt her; she’s a sweet, beautiful girl and makes me smile a lot, and understands me more than I feel like anybody else has. I should also mention that our friendship is online, which is another reason I don’t want to start dating her. I don’t have a great track record with online relationships.


Usually I would tell myself to just have fun and see where things go, but right now I fear that any relationship would become serious and end badly, so I don’t know what to do. She is also getting over a recent relationship.

Truthfully, taking a break from dating has been nice because it feels good to do what I want. I do miss being in love but, for now, is the flirting OK, if I don’t want to do anything else? Or am I wasting our time?


A. Flirting is fine. Messaging is fine. If chatting with this woman makes you happy during this difficult time, I don’t see any reason to stop. Just let her know what you want from the relationship. Make sure it’s clear that for now, the status quo is all you can offer. Both of you have to be on board with this kind of pace.


If the conversation continues for more than a few months, you should think about taking a risk and trying this in real life. It’s possible that if you get to know this woman in person, you won’t fall madly in love — and that’s OK. Or maybe you will, and you’ll think: Thank goodness I didn’t squander this opportunity!

As for the risk of getting hurt, there’s no way to avoid that. Chatting online forever can be hurtful, too. I don’t think there’s a way to care for someone without being open to all kids of feelings, good and bad.

For now, as you continue to explore this flirtation, pay attention to how much you’re communicating with her instead of people you see in the world. If she’s becoming a path to escape — if you talk to her so that you don’t have to show yourself to anyone else – it’s not healthy.



I realize this is 2018, but an online relationship of any categorization, even friendly/flirting, is not rooted in reality. It’s a fairy tale. Humans interact physically in real life to really get to know each other, it’s a crazy concept that was all the rage back before the Internet. Why are you overthinking this? I assume it’s because you have not processed the breakup (or you could just be a drama queen, there might be that). Go live your life and stop obsessing over what-ifs.



This on-line relationship is just an escape for you. Maybe that’s OK, but if you want more than that, you are going to have to try to date this person, in person. Yes, it very well may end badly, but almost all relationships do end badly, for at least one of the people involved. Rather than worrying about the end, think about whether you would enjoy the part before that.


I liked messaging/flirting back when I wasn’t quite ready to date. Turns out there were a lot of people who felt the same way. In fact, when I was ready to date I was annoyed that so many people I met online seemed perfectly content with never meeting. The point is, if you are enjoying it for what it is and she’s on board, keep going. If you are avoiding what you really want from her (i.e. a relationship), then maybe it’s time to “woman-up” and face your fears.


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Column and comments are edited and reprinted from boston.com/loveletters. Send letters to meredith.goldstein@globe.com.