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Date a friend and best friend's ex? Need unbiased advice.

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I'm racking my brain about this little problem of mine but don't want to talk about it with my friends just yet, since me and the girl in question share all of our friends.


Anyway, so I just got out of a long relationship... over 3 years. She was living with me. We broke up in a kind of messy way, and in one of our arguments she commented on my "love affair" (her words) with 'Amy'. I thought it was odd, since 'Amy' and I had been friends since gradeschool, and I only thought of her as a friend all these years.


She left about 4 months ago now, and since Amy and I are the only singles left in our group of friends, we naturally clung together. During the past 4 months, I've been seeing Amy more and more as a girlfriend and less and less as a 'regular' friend. I suspect she feels the same. When we go out, she loves holding my hand and sitting as close to me as possible. When we stay in to watch a movie, she loves cuddling up close. She's started insisting I switch from calling her "dude", as I've done for many years, instead wanting me to call her "babe".


If this was my only problem, I would have fessed up and made my move a few weeks ago.


But no. My best friend, 'Brad', cheated on his current fiance with Amy. It was an affair that lasted a few months and nearly destroyed mine and his friendship. Brad and Amy remain friends, albeit hostile friends, all these years later. I'm the best man in Brad's wedding next year.


I'm not at all eager to tell Amy or Brad about what's going on in my head for reasons that should be obvious right now. I never thought my life would have soap-opera like drama in it, since normally I'm the type who avoids things like that (no, seriously). Most of my friends, Brad excluded, tell me I should just go for it and 'stick it in her' (my friends aren't the best with words), and I casually brush it off, careful to not dismiss or confirm that I have a bit of a crush on her.


So what do you guys think? Any advice for a guy whose probably putting too much thought into things?

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OK, your ex does not seem to complicate the issue. If I am wrong about that, correct me.


The only thing that does complicate the issue is a fling between Amy and Brad, which involved him cheating on his fiance. Right?


And it does not really seem to comlicate things for Amy, because she definitely seems interested in you.


So Brad is the only issue, right? The question seem to be how he reacts when he finds out that you and Amy have a thing going on, or if you ask him. Did I break things down the right way?


Can you ask him in the manner that you friends imply? Instead of going up to him and implying you want her to be involved with you, why not present the question as if that is not the question. Say you talk about how since you broke up with your ex, you are in need of a little satisfaction and tired of having you way with yourself. And end fit in there a question about "So are you going to be pissed when I tag Amy to relieve my urges?"


I am just trying to think of a way to ask without making it seem like the question you are asking is what it is. You don't seem from your post to just want to get off and them look for someone else new. You seem to have soem serious intentions.

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My ex is uninvolved, except that she recently started dating another guy and I've been looking at Angie a little more seriously since I found that out. You're right in your assumption that I'm not thinking of Amy as a fling... I think we'd be good in the long haul, since we already have the friendship thing down pat. She deserves much better than to be a rebound chick.


Brad is the only real issue, since I'm sure both Amy and I would give the relationship thing a shot if it weren't for him. Even though he's getting married, he does give me dirty looks and doesn't seem at all pleased when Amy and I flirt around and are even the least bit affectionate in front of him. He almost seems jealous and angry. I haven't talked to Amy or Brad about this behavior.


The "relieving my urges" line won't work, since he knows I haven't been a one-night-stand type guy since college, and certainly not with a good friend. However, you may be onto something with the indirect approach. Maybe get a couple beers in him and say something like "Man, wouldn't it be weird if Amy and I got together?" Now to figure out a way to get that to fit into a conversation.


Thanks for the reply. Any more help is definitely appreciated.

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Yes, and I would apporach it from the less serious angle. It lets you figure out what he is thinking wihtout him knowing what you are thinking.


Although, you have to know you are treading on thin ice with your friendship with him. Mostly, I see this because there is going to have to be soem tension between Amy, him and his fiance, soon to be wife, forever. If you have that tension, then it won't be easy to remain friends. Of course, if things were good with Amy, it should be worth it.


Feeling him out in a joking manner gives you an idea of what will happen before you jump.

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I'd say go for it with Amy. Forget about Brad! He's getting married!

So he has absolutely no right to act like you and Amy can't be together.

Amy is not his fiance! He does not "own" her nor does he have any right to tell you who you can and can't date. If Brad is really that upset about you and Amy seeing each other, then he probably should not be getting married. This may seem weird but I would flat out ask Brad how he feels about Amy. Why did he choose her to cheat on his fiance with? Why did she go along with it?

You could say something along the lines of, " I know you are protective of Amy as a friend, but I'd really like to take her out and see where it goes."

If he reacts badly, remind him that he's getting married and has no claim to Amy romantically.

Bottom line: If you and Amy like each other, you should give it a try. Brad has chosen to get married, his choice, end of story.

Good luck.

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Beec> I know I'm treading on thin ice, which is why I'm not really doing anything as far as "making my move" goes. I'm worried we'll end up being victims of inaction.


Brad and Amy are hostile friends already. There's already strange tension between them. I don't want that to spread into my relationship with Amy OR with Brad, however.


York> Logically, you're right. I'm just worried because I know when it comes to relationships, a lot of logic goes right out the window.


Why did he cheat on his girlfriend with her? Well, we were all around 20 years old at the time... stupid and young and drunk most of the time. I don't have an answer besides that one. I'm sure they had some amount of feelings for each other, but that's kind of a forbidden topic. They never want to talk to me about it, which is fine. Unless I start dating Amy, in which case, I think I need to know.


I do agree with your bottom line. I'm 90% sure I'm going to go for it with Amy, but figuring out how to do it without pissing off Brad beyond repair will be tricky.


Thanks for the input, guys. Much appreciated.

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OK, now you laid it out.


My plan: 1. break into the topic with Brad. Smooth over the idea that you and her should be none of his business; 2. Get with her, keep it hidden for a while, be discrete; 3. Break the idea with her that you know what happened between them, it doesn't bother you, but you don't want to lose his friendship, which means there needs to be some peace between them; 4. try to get peace, if not enjoy being with Amy.

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  • 3 weeks later...

Alcohol: The answer to all our problems.


So last night Amy called me from her office Christmas party saying she and a few friends were going to go to a local bar. She was out of her mind drunk. I was completely sober. I ended up going out.


It was a long night of her hanging on me and hugging me nd wanting to talk to me with our foreheads touching. I chalked all of it up to her being drunk and needing balance, plus we ARE affectionate friends.


When she started kissing me on the cheek incessently, I started to get suspicious. When she started kissing my neck, I knew something was up. Finally she looked me dead in the eyes and said "Tom, I love you." Only she didn't say Tom, she used my real name. I replied "Yeah, I love you too." She said "No you don't. Not like I love you." I thought it was a strange conversation, but didn't take it too seriously because she was wasted. A few seconds later, she put her tongue in my mouth. We made out pretty seriously for about 30 seconds before I stopped, figuring she would feel silly today 1. for making out with me, and 2. for doing so in front of all her coworkers. We repeated the event 2 or 3 more times before the night was over.


So this means we definitely need to have the talk, and probably soon. Things are coming to a head. Thanks for the help guys, but I guess the ultimate help came from a few bottles of beer. Is there anything alcohol can't do?

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So, I've tried a few times to talk about things with her. She uses the "black out" card, carefully denying that she has no recollection of anything that happened. I told her about the kissing, and she wasn't too shocked. Whenever I tried to mention the talks/confession, she closes up and says things like "I bet I said a lot of stupid things", or "I don't think I need to know exactly what happened that night."


Things aren't awkward between us at all, though. We just act the same as we always did, except I joke more about her kissing me. She takes it well. No uncomfortable moments or anything, which is nice.


Still, it bothers the hell out of me that I know she has a crush on me, and I know I'm interested in pursuing things with her, but neither of us has the balls to make it happen. I'm halfway scared that I'll bring up the subject and she'll say she was wasted and her coworkers were egging her on and she didn't mean it. Then I look like an idiot. And I'm halfway scared that she'll say she has a crush on me but nothing can happen because of Brad. She did warn me to not mention the kiss to him for fear of him overreacting and "freaking out".


I need to figure out a way to bring it up without putting either of us in an akward position that we can't get out of. I don't want to corner her get myself cornered into saying something I don't want to say. Now it's just finding a time and figuring out how to say it.

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