David R. Herz: for Men

How does a handsome male in his 40s, who has been celibate for over 10 years, get back into dating?

I had a few abusive relationships and decided I was better off without a girlfriend in my life. Now I would like to try again. But I am so rusty and awkward with my flirting and dating skills. And I'm pretty sure being honest with a woman about my situation is a bad idea.

The best thing to do is just to start. You will make mistakes. You can’t get better if you are not in the game.

However, you also want to look at what it was about you that you found yourself in a series of abusive relationships, or at least set up some really clear red lines so that if an abusive relationship shows up again, you can end it fast. And if there is anything incomplete about those past relationships, complete that now (use this: How to Leave Your Ex Behind).

And honesty is sexy, but do not enroll people in how pathetic you have been or are. Just deal with what’s so and what you are up to, maybe like this:

“I was in a couple of bad relationships, and I gave it way too much meaning; so I checked out for a while. Now I’m back, and I’m committed to having a magical relationship. And I’m afraid I’m a little out of practice.” and then just shut up and see how she responds.

And I wouldn’t worry too much about flirting and dating skills. The best thing to hone is your listening skills. No one really listens, but everyone wants to be gotten.

I don't think it's wrong but a friend does. There's a girl I think is cute. I flirt with her a lot and she has a boyfriend. He thinks I'm wrong for doing so but I don't see the problem.

No problem at all from your side. It might not be the best move for her.

Here, I’m going to make up some rules for flirting with another guy’s girlfriend:

1. Make sure her current boyfriend isn’t going to knock your block off if he finds out.
   
2. Set clear boundaries for yourself. For instance, don’t let it go beyond flirting unless she has first completed her relationship with her current boyfriend. You wouldn’t want someone to cheat on you. And you probably wouldn’t in the long run want to be with someone who can’t be honest.
   
3. Before you flirt with her, ask yourself if there isn’t really someone else you should be flirting with. It seems kind of stupid to waste your energies on people with low relationship potential.