This particular situation has an incredible amount of backstory so I’ll speed through it a bit for you.

I (22M) broke up with my ex back in Fall last year – we had dated for 7 years. In the middle of those 7 years, I met a (22F) girl (let’s call her G). We became really close friends, too close. I emotionally cheated on my girlfriend at the time with G. Nothing physical but a few months of spending constant 1 on 1 time, going out, confiding in each other, etc. and we both admitted to having feelings for each other.

Eventually my girlfriend at the time found out and so I cut off G and we spent the next 3 years hardly communicating, only seeing each other through mutuals – which sucked because we were very naturally connected to each other and never stopped getting along so well.

Then G got a boyfriend in early 2022. When my girlfriend dumped me in September, I reached out to G and we became friends again (because of that natural connection that was never lost). My feelings slowly started to build back up but we didn’t spend nearly as much time together because G had a boyfriend.

However, G just dumped said boyfriend a few days ago. She’s kept me in the loop about the whole process so we are quite close again. We text everyday, have been comfortable seeing each other 1 on 1 the last couple weeks, etc.

I feel such an incredible connection with her that I hate not taking the opportunity now to finally ask to take her out as we’ve never had the opportunity before this.

How long should I wait since she just broke up? Is this even a good idea in the first place given what our relationship has gone through? How do I even go about telling her I feel this way?

1 comment
  1. You miss 100% of the shots you don’t take. Go for it! Best case: you vibe; she’s your new girlfriend. Worst case: she says no; you move on…no unanswered questions, no regrets.

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