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I like one of my ex-boyfriend's friends. (Me and my ex have a lot of the same friends.) I've never hung out alone with this friend, just in group settings. What should I do?

Ah, the ol' friend switcheroo. It can be tricky, because it means potentially spending time with your ex. Even if you're close friends with your ex and there's zero jealousy involved (which does happen, believe it or not), there's always the potential for awkwardness.

The trick is to get this guy alone just as you would any friend in your social circle, and ignore fact that you know him through your ex. Treat him as you would any friend who you're interested in, and try to engineer some alone time. If you are out in group, turn the flirt on and try to get him to grab food or a drink with you away from your ex and other friends. Hopefully he'll take the hint.

You could always just go for it and ask him to hang out one-on-one. Email, IM, or Facebook would be a good way to break the ice and establish a relationship away from your circle of friends. If you're shy, mention you've been waiting to try that new Thai place, or see Toy Story 3, and see if he takes the bait.

What do you have to lose? Worried your ex will get jealous? He's in the past. (If you are worried about your ex's feelings, then you probably have some unresolved emotions of your own and shouldn't be hanging out with him socially in the first place.)

If the guy is your ex's best friend, be prepared for some initial weirdness. Best case scenario, the guy is more of a casual acquaintance who doesn't want to spend a ton of time with one of your exes. (Hopefully the new guy won't be put in a situation of having to decide between you and your ex, but if that does happens, fingers crossed it comes out in your favor.) When you do start dating, definitely try to avoid hanging out with your ex early on. Let the relationship breathe and build without his influence. Oh, and this probably goes without saying, but try not to talk about your ex on the first date (or in bed). 
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I'm actually in a similar situation. The only difference is that I like my friend's ex-girlfriend. She lives about an hour away from me, but that's not really the problem (I am more than willing to commute). I don't know if she likes me or not. There were times over this past summer when she said she wanted me to come visit her with some of my other friends (excluding her ex), but I couldn't because I had to study for the MCAT. I wish I could go back and change my decision. I know she is extremely busy at work (working apx. 50 hrs a week), so I'm hoping that because she didn't respnond to my most recent texts it's because she is just too busy or tired to do so. She dated my friend for several years, but they have been broken up for around 1 1/2 to 2. I'm not worried about his reaction; I just don't want to be too forward and ruin my great friendship with her. No matter what I try, I can't stop thinking about her. I really do love her. Of course if I told her that I'm sure she would freak out. To be honest, just replying to your post is a bit of a relief for me. All in all, the best advice I can give you is to be completely open about how you feel. My entire being aches with the thought of her being even remotely close to feeling the same way. I've been gradually develping feelings for her over the past 5 years (which I feel guilty about due to the fact that my friend and her were still together). I don't know how much more of this I can take. I never even knew I could feel this way (the proof of which is this response; I've never responded to another person's random post before). I hope this is more than incoherent babble to you.

Sincerely,
Clueless

P.S. Sorry about the rambling.

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What do you do when your ex's friend is going to be living with your ex? Or how about when you and your ex's friend both really like each other and are both too selfless to put any of their own desires before the happiness of another soul? What do you do when you both feel like you've made so many mistakes and just don't want to cause anymore calamity? Yet, you're the only ones who truly understand one another? What do you do when you both hang out with your ex?

It sucks. Part of you wants to just let it go and engage in this new relationship, but the rest of you is too conscious of the consequences your own actions may bear on the third party.

What's the right thing to do?

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Thanks, Heather! I hope you're doing very well. Maybe I'll see you around town soon?

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598022 575908The Spirit of the Lord is with them that fear him. 216822

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