and move on. Chicks are like busses, another one comes along every 10 minutes. So what. He had a young piece and now he is broken hearted. Go to Vegas, both of your and party. Tell him to lose her number, forever, and never call her or return her calls. She is doing exactly what she is supposed to be doing.

That's it. End of story. She was stupid to be dating him in the first place, and she was smart to dump him.

One word:

Casseroles.

LW,

What a good friend you are. He may be wrecked right now, but is quite fortunate to have your friendship. Cary's advice sounds right and I would add: Be prepared for some roller coaster emo boy behavior. Maybe he'll recede, maybe he'll act out, who knows. Just know it has nothing to do with you and stay firm and supportive. Love your friend now.

I had a friend let me have her house for a long weekend once when I was hurt. Instead of rolling up the sleeves and working on it, really letting the feelings sink in, I went out, and drank... a lot... and did some other ignorant, forgettable things. So, Cary is right on that too. Escapism will only make the wound deeper.

Your consolation may save him from himself. I wish you well.

she's not coming back? maybe at 41 he's been around the block enough to recognize when there's a true connection (vs. some fling or a mismatch). i know she's almost 20 years younger but it is possible that they were really in love. in which case, maybe they'll find their way back together? am i just being naive?

She's not coming back, because she's already hooked up with another sugar daddy. Come on now, a 19-year-old single mom who finds a 37-year-old old fool to take care of her doesn't leave till she's found a (better) replacement.

Wow! The age difference seems to have bothered more respondents than the situation. The femme in this breakup is not a minor and she wasn't when she got involved with the guy she's now leaving. Interesting the amount of moralizing going on here when the question was how can the LW help buddy boy get past this catastrophe. I do believe he's got some issues, but the age difference isn't one of them.

Cary gave really good advice and, as per usual, did not pass judgement on the (adult) people involved. Good show, although Cary's sometimes non-judgemental to a fault. Not this time, though. Of course, I'm a perv by the standard set forth by some of the replies, since I wouldn't rule out a relationship with a woman because of such an age difference alone. Then again, if it didn't work I'd feel the reason was a clear and present danger all along, and would be accepting.

There are good reasons why a 41 year old guy probably shouldn't date a 23 year old, and the letter to Cary pretty much says it all. There's just not enough common ground in most of these relationships. Later, though, it improves. This is why I'm not horrified that Fred Thompson is married to a woman 24 years his junior. I don't think that's what will keep him out of the White House, either.

But the LW's question was fielded quite well by Cary (and on the fly, no less!). Give credit where credit is due and pass on the judgement passing!

I can't muster sympathy for your friend, because an 18 year age difference, when we are discussing twenty year olds and forty year olds, is almost without exception doomed to failure with few very rare exceptions. I am surprised your friend would invest so much into such a young person who is obviously immature and still in a very different stage of her life. It's also very hard for me to imagine that they had much to talk about in the first place: what were the common intellectual interests? mutual friends? taste in art and books? Your friend strikes me as terribly insecure and young for 41.

typos, argh.

This guy has major issues, and being left by an immature young woman who had a child when she was sixteen may be the least of them.

It's funny we discuss steps to getting over a lost love like it's putting up shelves.

Here are mine. Step one: it hurts. Step two: it sucks. And it's going to hurt and suck for a while. And even after you give the last of the departed love's things to goodwill, you are still giong to pine for her. That's part of it too. That's life. Feel it. Live it. And eventually it passes. There's no "30 Days to Getting Over Her" or "Heal that heart in 1/2 the time or your money back."

If he broke his leg and though set properly it didn't heal in exactly 6 weeks you wouldn't tear off his cast and tell him to go jogging.

The best thing you can do is be a friend and let the guy heal at his own pace.

<41 year olds shouldn't be dating 23 year olds. That's it. End of story. She was stupid to be dating him in the first place, and she was smart to dump him.>

Don't be so annoyingly sanctimonious. Older men and younger women will always date because men are biologically programmed to desire youthful attributes, and women are biologically programmed to desire power and wisdom. And thank God! I'm 38 and am looking forward to my golden years in all their glory.

Sorry babe, but when it comes to gender issues mother nature trumps all other concerns.

She's not coming back, because she's already hooked up with another sugar daddy. Come on now, a 19-year-old single mom who finds a 37-year-old old fool to take care of her doesn't leave till she's found a (better) replacement.

I knew I’d find a putz or two afoot as soon as I’d read this letter, but this one’s really got them crawling out of the woodwork. Yup, there’s nothing more adorable than those who conflate their subjective aesthetic preferences with universal moral imperatives. In other words, because they’re repulsed by the notion of dating someone 20 years older, doing so must be immoral, wrong for everyone else, and inevitably doomed to failure. Such puritanical, self-absorbed assholes ought to consider a philosophy of life others have found enormously worthwhile: it’s called “live and let live.” Don’t like pornography? Don’t watch it; don’t approve of abortion? Don’t have one; don’t like taking it up the ass? Don’t do it. Otherwise, mind your own goddamn business and don't worry about anyone else's preferences, unless they involve violence, cruelty or abuse.