So I'm in a bit of a dilemma. A good friend of mine, whom I've known for over 5 years or so now, dated a girl in high school. They were in 'love', blah blah blah, etc. Broke up after about 2 years of dating and it did not end well. We're now both in college and I began talking to her on a regular basis a few weeks ago. We seem to connect significantly better than he did with her. And I truly like her, so this isn't just a one night stand scheme. My good friend and I are still good friends, but you know how college tends to phase some people out over time. I feel like this is happening to him and I so I don't feel as terrible as I thought I would about seeing her, but in the back of my head, I'm absolutely positive he still has feelings for her, no matter what he says. So my options are to either cut it off with her before something bad happens, or come clean with him, accept whatever harsh words he may say, and possibly lose him as a friend. I really do care about her and I can see it going somewhere, although I said that about every other serious relationship I've gotten myself into and none of them ended well. Comments? Advice?

Have you even talked to him about it? Now you don't have to, your not dating his daughter or anything but if your trying to maintain a respectful relationship with him then it's probably a good idea. I have done this for girls in the past that my friends got serious with, it's usually about a minute conversation and leaves both parties feeling satisfied.

If he's a mature person and most importantly a good friend then he shouldn't have any problem with it.

"You know I have really started to connect with so and so, I know you two have a past together and I'm interested in having a future with her, I hope this won't infringe upon our friendship blah blah blah"

Alright, that was a bit cheesy but it's a rough guideline. I've been in this situation before and it's never really serious, I think your just blowing it out of proportion.

Good luck.

Which do you value more, his friendship or a possible relationship with her? Pick one.

Ya. Also, I would recommend talking to her before ever talking to him.

You need to know what she really thinks of the other guy. If there is no chance of a relationship between them ever, then your friend has nothing to be mad about.

Most likely, it will end badly for you, and the relationship wont last. You know this.

But there is always that small chance.

Sadly, you're right. There are plenty of other women out there and I attempt to remind myself of this, but you know how it gets when you find someone you're ridiculously attracted to.

Why not ask him how he feels about you dating her? If he's ok with it, great. If not, then I'd take a friend over a girl any day.

Be very, very careful about this. Talk to the girl and find out if the two of you really want to pursue a relationship. If you do, talk to your friend and see how he feels about it. You don't need his permission to date her, but you'll feel a lot better if you talk to him about it. If he's not cool with it you'll be in a pretty unpleasant situation. If he is, you still have to be really careful.

I was in this situation a while back, and I did end up dating the guy. His ex/my friend was happy for both of us...for the first few months. After that she went batshit insane and became a total bitch. I nearly lost my entire group of friends because of her...

If you're ready to lose your best friend over this girl, then go for it.

Friends don't always last forever, and if this girl is more important to you than him, then he'll just have to accept the hard facts. Some things are more important.

Normally I'd be saying this is wrong, etc. and not to do it. But if you're willing to lose your best friend over a girl, then she's got to be important to you, so I can't come in here telling you not to do it.

Just be sure you're willing to do it, even if you're still friends afterwards, just know that it's a possibility that you could lose him as a friend.

Yeah, honestly, I really think I'd much rather keep him as a friend. I'm most likely going to let her know we can't continue talking some time this week.It's just going to be difficult to break it to her since she's grown to like me a bit more than I have her.

It was secondary school. He was bound to have strong emotions for her, the kind that you can never fully justify. Do not go their, it will kill a bit inside of him and ruin a friendship.