I met a guy that I really like. We connected immediately and both began dating. He told me that he briefly dated a close friend of mine once he happened to see a picture of my friend and I on my FB page. Briefly was a few dates and sex once when they were freshman in college. We are now 35 and she says that she has no interest in him- she has a boyfriend and a strong relationship with him- and he says that he has no interest in her, but that he thought that I should know. My question is, should I continue to date him and how can I make sure the situation is not awkward when we are all together?
I had to put myself in your situation to answer this question. I personally don’t think I would date any of my best friend’s ex-partners but that’s just me. You may have a total different relationship with your friends than I do, so it would be hard for me to judge. However, I guess you need to value your relationship with your friend and confirm the extent of her feelings for this dude past and present. If your friend totally gives you the green light then go for it as long as everyone is on the same page. One good thing you can get out of this situation is the truth about your guy friend. I’m sure your girlfriend will tell you the good and bad about him so you can make a better judgment about the potential relationship. I would weigh out the pro’s and con’s of this situation and try to make a good decision without damaging any friendships or relationships. The fact that you are asking about your situation makes me believe that you are battling with this issue and you are trying to make the right decision. Go with your gut and initial instinct!
You all are adults. They guy you like and your girlfriend are aware of your dating situation, and if they are being honest, have no desire for each other. So, that means you have a green light to continue seeing him, if that is your desire. As far as the awkwardness, the best way to deal with that is to address it, but it sounds like you have done that already. There is nothing else more for you to do. If a situation arises in which you feel awkward, acknowledge it and be willing to let it be. Over time, the awkwardness will diminish, once you continue to receive confirmation that all is well.
You all are grown now and that relationship/ interaction was more than fifteen years ago. If it had been something serious, then I would say I would reconsider. But it sounded like something completely casual and since both of them have moved on, there really should not be problem. He told you up front and that says a lot. Enjoy your relationship. Your friend is enjoying hers. Everyone is somebody’s ex.
From the Male POV ~CJ
Honestly, as a 35 year old woman, you shouldn’t concern yourself with freshmen year drama. If you like this guy then accept that they dated FIFTEEN YEARS AGO and move on. Don’t subconsciously sabotage the relationship by getting caught up on something that is a non-factor to them but is a big deal to you because you’ll look insecure and immature to harp on something that happened FIFTEEN YEARS AGO.
Situations will never be awkward if you:
1) let go of freshman year drama
2) focus more on establish a new unique relationship that is unique to you two. She nor any other women will be a blip on his radar if you take the time to get to know him and his interests and how you two can establish a unique dynamic.
Stacey
Caramel Lattes & Stilettos
Crys2Sana
Hilda Fields
lisalee425
caramellattesandstilettos.com 
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