We’ve talked on and off for a few years. Is it worth a shot?

[Anonymous]

Matched with this guy on an app, good convos initially but then it somehow fizzes out by lagging responses or either of us deleting the app. We’ve done this a couple times now over the last two years and currently it’s back on, and something he always brings up is the fact that we keep matching over and over even after all these years, so it must mean something.

I wanna address the pattern because it’s all fun and light to talk to him but I eventually want a serious relationship and I’ve always put off the convo of what are we doing here because I was afraid of coming off pushy. But I’m in a better place to where I feel confident enough to bring it up, no matter the response.

I can’t tell if it’s just a line a guy says to girls to keep them on a string or if he feels that we could be something if we try it out, I still have trauma from my past lol what do you think?

Side note: we have met in person before because we use to work at the same company but it wasn’t until we crossed paths at work for a little bit that he left for a different job.

[Oliverlogan263]

Hmm that's definitely a tricky situation. On one hand, it could be a good sign that you guys keep matching up over the years, like maybe you're meant to connect somehow. But at the same time, all the on-and-off talking without really making plans to meet up would for sure make me question how serious he is about following through on anything.

I get being afraid to come off pushy, but it's totally reasonable for you to want some clarity on where things are going after so long of talking on and off. I'd say go for having an honest conversation with him, but maybe try to feel him out a bit first on his plans when you do meet up next. Like ask what he's looking for on the app, if he's dating other people too or interested in being exclusive with someone, what his ideal relationship would be like one day. His answers to those types of questions might give you a better idea if he's actually ready to commit or just enjoys the attention.

And don't get too discouraged if he doesn't give you a clear yes right away either - people can be scared of commitment sometimes even if they like someone. As long as he's willing to have real conversations about both of your needs and takes time to build trust in person, it might could work out. But you gotta follow your gut too - if after trying to talk it through more you still don't feel good about it, then don't force yourself to keep going just cause you like him. Hopefully he'll treat you with care and respect either way. Let me know how it goes!

[Avicenna]

Sure, why not? There's nothing to lose.