I would tell him that my friends, family, colleagues are off limits. And that he can disrespect his spouse but not in your home.

A bunch of losers on this board srsly. I just don't understand this "not my problem" culture.

Talk to your friend OP. If he isn't thick in the head, he'll get the message about how he's hurting his wife. Men are dumb like that sometimes.
I would kill to have a friend like you. Ignore the losers.

Anonymous wrote:

Anonymous wrote: he has tried to sleep with me in the past but I was firm that I'd never go there with a close friend and he respected that

Guy here and you need to know this statement is bullshit. He doesn't respect you, he doesn't respect other women, and he sure as hell doesn't respect himself. He sounds like a dick and there's no reason for a woman to have a man for a best friend outside of a romantic relationship. Because if you're not in a serious relationship now- as soon as you get into one your friendship with this guy will be a problem.

^This!

I had a male friend exactly like OPs. He was a total hater when I got serious with my now-DH, had a panic attack at our wedding (seriously), and cut me off when I gave birth. All this even though he had a significant other!

On a different note, I don't think OP's concern is for the wife or morality. I think OP has a thing for this guy and is jealous when he flirts. People often dress up their baser instincts as "concern" for others. You're just a liiiittle too invested though. Not buying it.

My good friend is the same way. I accept him for who he is. He treats me with respect and is in therapy. He isn't married, but if he were I would absolutely call him out on his behavior, but we have that kind of relationship.

Anonymous wrote:I would have dropped this friend long ago.

I kind of agree here. Why are you such good friends with someone who so clearly does not value relationships or women? I'm not judging here just asking. Perhaps if you answer that question first you can better answer the one you opened this thread with. In other words, do you thrive off the drama this creates? The sexual tension that it fosters between you? Or do you like to fix people? Or have you had this same man in your life in other ways--father, bf--and are compelled to repeat the cycle? Anyway, it seems like if you truly knew him you would have known this was coming from miles away and known you either bail on him, or hold your tongue. No one wins if you try to play superhero friend to the rescue here.

Anonymous wrote:Let his wife worry about this. You sound like a character in a bad Julia Roberts movie.

Excuse me, but "My Best Friend's Wedding" is an awesome movie!!

I googled this because I'm dealing with something VERY similar, and OP has described my situation so eerily that it's almost spooky. My cousin (a guy) and I have been best friends since we were kids and he has always been a huge womanizer, and now I see him heading towards a very expensive divorce due to his womanizing ways and I'm very worried for him.

Being friends with self-destructive men like this can be exhausting emotionally.

I had a friend like this, just exactly like this! For a while everyone thought he was gay. He's not.
Anyway, he's divorced and lonely now.

The real issue you're struggling with is boundaries, OP. You're trying to frame your involvement in your friend's life as something other than over-involvement. It is over-involvement, though. Your post here on DCUM is Exhibit A. Exhibit B: your friend whose problems with boundaries is the subject of your post. It's no coincidence that your friend shares your problem with boundaries.

He is a grown adult and you are as well and you both have your own individual lives to attend to.

I would simply let him live his and try hard to ignore everything that he does as long as it does not impact your own life in a negative manner.

Remember: Karma never forgets a soul.

Unfortunately, OP, you can't really say anything. Mostly because your friend still wants to sleep with you. If you were his best male friend, I'd say call him out, but you can't do that because there's probably some sexual tension between you... whether or not you'll admit it. Distance yourself from these situations. Try to support your friend in his quest to become a better person.

You just salivate over this, don't you? He's never going to leave his wife for you.

Anonymous wrote:

Anonymous wrote:I would have dropped this friend long ago.

Life isn't that simple. A man can be a bad boyfriend or husband, but a very loyal friend. He's been a good friend to me - sometimes he's selfish as a friend too, but when I ream him out for not doing his duty sometimes (standing up for me, or telling me what other people have said about me for example), he always corrects himself. We have joked about being brother and sister in the past and 90% of the time he comes through for me.

People are complicated, unfortunately.

I don't know if I'd drop him, but I'd say something like "Look, you're on of my best friends and you've always been there for me. You did some stuff as a single guy that I didn't really approve of, but I figured it wasn't really my business. It makes me uncomfortable that you flirt so much with other women while you're married. I can't support adultery, and if you cheat on your wife, I don't think our friendship would survive that. "

Anonymous wrote:

Anonymous wrote:I would have dropped this friend long ago.

Life isn't that simple. A man can be a bad boyfriend or husband, but a very loyal friend. He's been a good friend to me - sometimes he's selfish as a friend too, but when I ream him out for not doing his duty sometimes (standing up for me, or telling me what other people have said about me for example), he always corrects himself. We have joked about being brother and sister in the past and 90% of the time he comes through for me.

People are complicated, unfortunately.

If my brother were a jerk, though, I could still decide not to be friends with him. So can you.

Anonymous wrote:I would have dropped this friend long ago.

Life isn't that simple. A man can be a bad boyfriend or husband, but a very loyal friend. He's been a good friend to me - sometimes he's selfish as a friend too, but when I ream him out for not doing his duty sometimes (standing up for me, or telling me what other people have said about me for example), he always corrects himself. We have joked about being brother and sister in the past and 90% of the time he comes through for me.

People are complicated, unfortunately.