Ask A Guy: Should You Date Someone Who Just Got Out Of A Relationship?

Photo Source: iStock

Photo Source: iStock

Hey Joel,

I’ve been friends with this guy who I like for a year. He had a girlfriend, but when he found out she was cheating on him, they broke up. Then two days later he told me he’s always had a crush on me, but he thinks I like my ex boyfriend. I told him I don’t, but he’s gets jealous when I talk to him. I asked him why, and he said it’s because he just doesn’t want to be blown off again. I told him I liked him, and he asked me out. His ex found out and she now hates me. Should I date him?

My initial reaction is no, you should not date him – right now. From everything you’re saying, it seems like neither of you are in a great position to be in a relationship at the moment, but that can easily be changed over time. Both of you still need time to heal from your previous relationships, as you don’t want to be his rebound – and we’ll discuss your ex in a bit.

You need to understand that this guy got cheated on, and speaking from experience, that isn’t something ANYONE forgets very quickly. Even though you had nothing to do with his ex being unfaithful, that memory sits in the back of his mind in future relationships and can make him emotionally unavailable for a bit. It won’t ALWAYS be there, but because it happened so recently, it’s going to be tough for him to trust.

Chances are, his initial reveal of his feelings for you were a bit of a reaction to his breakup, and while it doesn’t mean he wasn’t serious, I would take them lightly for now. Again, you both need some time and space, and letting things build naturally is the best option.

It is a bit odd that both of your exes seem to be adding more drama to the situation, and I wonder why you haven’t cut both of them out of your life already. Unless your ex is a really, REALLY good friend of yours, it is very difficult to navigate the boyfriend-now-friend gauntlet. In many cases, this can turn off guys who are a bit less confident, as they think you’ll always be reconsidering your ex. Right now, you’re throwing mixed signals by having your ex in your life, so if he’s just a periphery friend, cut the cord and move on.

Insofar as this guy’s ex, who cares what she thinks of you? If she was your friend beforehand, then you shouldn’t have been going after him in the first place. If she wasn’t your friend, then it shouldn’t matter if she doesn’t like you now?

In the end, if you want to be with this guy, then you need to let things breathe and take their natural course. If you jump into it right now, he’s still going to be fragile from getting cheated on, and that will add a great deal of unnecessary stress. Just relax and let things build naturally, and If it was meant to be, it will get there when you’re both ready.

Best of luck!


Joel Freimark has done a lot in life and seen even more. From last minute international travel to bizarre places to writing award winning books, he’s here to bring his wisdom to all your problems. He hosts a weekly advice series on Youtube and a music series also on YouTube.. No question is too outrageous or personal, so go ahead and fire away! Follow him on Twitter.

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