Should he and I date again?

For the past 3 years, give or take, I have dated a boy occasionally. Every time we obviously broke up but it is always because I end things once they got serious and every time that happened the boy said he would wait for me. I have always had feelings for him but sometimes I doubt they are as strong as his feelings for me so I end up feeling bad.

The first time we dated I broke up with him because we dated right after I had gotten out of a relationship and I was still kind of hung up on the guy I last dated so the boy said he would wait for me until I was ready.

The second time we dated I thought I was ready but then the same ex I wasn't over the last time tried to start things up with me again and I ended up liking my ex again so I broke up with the boy to date my ex again which was a stupid mistake.

We haven't dated after I left him for my ex but we have hooked up countless times and recently I became close with him again relationship wise and I would love to give it another shot because I'm 100% positive I'm over my ex and this guy is literally the greatest thing ever and I feel bad for what I've put him through.

Should I ask him out and date him again or do you think it wouldn't work?


Most Helpful Guy

  • Tell him you're sorry for leaving him the first couple of time, and assure him that the feeling you have for him are permanent and you no longer have feelings for your ex, tell him what he means to you (without those words he'll be hesitant) and tell him you're ready and 100% sure! and if you guys can start over


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