Need an outsider's perspective, how stupid of an idea would it be to date this friend?

So I met this girl originally as I was dating her roommate and best friend a few years back. I introduced her to my best friend (and current roommate) and they hit it off as well for a time.

Since then we've all broken up but they've joined our friend group. We hang out pretty much every weekend and go to bars/drink/watch football together.

It's gotten to the point with this girl where all of our friends have commented at some point asking if there was anything going on between us. There's all kinds of pictures on Facebook of us together, even our own families have asked us (separately obviously). This last weekend she told me her mom asked if we were dating, and ironically enough the week before that my aunt had asked me the same thing.

And I realized recently I think the only reason we aren't is for the longest time I thought she was off-limits, as my ex's roommate and my roommate's ex.

This is a girl I trust with pretty much anything, loves many of the same things as me (heck we're going to a concert together in october) and constantly displays signs of affection like feigning falling asleep on my shoulder in bars or tackling me with a hug. I also definitely find her attractive...

But my roommate I think still has some kind of feelings for her even if he won't admit it (though he's been on other dates)... how stupid of an idea would it be to ask her out?

Yea, for simplicity's sake we'll call the girl I like Katie. I dated Katie's (former) roommate and best friend Becky ~3-4 years back, and Katie dated my roommate Alan, we've all been broken up for at least 2 years.


Most Helpful Girl

  • I think you should talk to Alan and tell him how you feel about Katie. If it is so evident now that you have that kind of chemistry, he might suspect something is going on (just as the people around you), and is better to check on his feelings first, but don't give up on Katie, sounds like a keeper!
    Doesn't matter what others may think, follow your heart


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What Girls Said 3

  • Wow the irony that she's your roommate's ex and your ex's roommate. I would tell you t o ask your roommate first for his permission and then see it from there. Good luck

  • I would talk to your roomate about it first to make sure it's okay. If he says that it is then I would definitely tell the girl how you feel. Based on what you said it seems that she may have feelings towards you as well.

  • Girls we have a challenge on hand but for some reason when I got to the end this one I am dying with laughter and for some reason it shocked the heck out of me. Girls can you help me out with some interpretation


What Guys Said 1

  • well its obvious your roommates priorities aren't set on him so I'd ask him and if he says no and ask him and if it sounds reasonable back down, but remember its her decision maybe she wants to date you. Then she should be the one to decide who she dates