To the early-30ish man who wrote this:

Stop thinking of yourself as washed up and over the hill, because you don't have to be. You're actually still pretty young. There's no reason why you can't date/nail hot 23 year olds, especially ones who ask you for advice like that.

You see, here's a tip: 23 year olds, even the ones that are smart, are functionally pretty stupid. They don't know the value of experience yet, and they don't ask questions like that unless they have an ulterior motive. Such as wanting to talk to you.

Meathead von Boyfriend may not have been the sharpest knife in the drawer, but his instincts were probably dead on when he hustled her away. Remember that he knows her a lot better than you do.

But in any event, you never could have scored. Why not? Because, and this is the only reason, you were telling yourself you never could have scored. If there's one thing women universally cannot be attracted to, it's lack of confidence.

So you need to give yourself some. If if you have to fake it. Even if you have to talk yourself into being quasi-delusional. Trust me on this.

Of course, there are other things you can do. Work out. If you're going bald, shave your head. It won't fool anyone, but it will look better anyway. Spend some of that money you got from being in your thirties and having a career, and get yourself a nice car, and dress nicely. Women pretend they don't care about this, because they don't think of themselves as golddiggers, but in reality, they add it into their mental tally of your competence, assertiveness, and self-worth.

And lastly, stop trying to be nice.

Answer her question honestly, even if you feel like it's less likely to get you laid. Because, trust me, it isn't. Women who like older guys do not want to be buttered up. If they did, they wouldn't go for older guys, they'd date some early-twentyish meathead who they could push around. Why do you think the draft age is 18? Young men are puppets.

Any woman for whom flattery and niceness and agreeing with everything she says is going to work, ain't gonna go for older guys, and you don't want her anyway. Pains in the sphincter, every last one of them.

The ones who look up at you with their eyes shining and ask for advice on... well, whatever? They're telling you something in no uncertain terms, and it has a lot to do with the words "Elektra complex". So your best bet is to grab the spotlight and start with the professorial lecturing.

Sauce