Should she stay or should she go?

Q: I’ve been dating this guy for about four months whom I’d dated before for almost a year. I ended it the first time because I felt he was not ready to commit and I was. He said he didn’t think it would work financially because he does a lot for his three kids. He is 14 years older than I (he’ll be 50 this summer), fairly successful in his work, and divorced. I’m a single mom with three kids. During the year we were apart, he was all I could think about, so we started dating again. The more time we spend together, the more my feelings grow. But now I’m starting to feel again that this relationship is going nowhere. He never talks about the future with me. I get the feeling that I’m his “secret” because I have yet to meet his kids or other family members. Should I cut my losses or hang in there a little longer?

Steve: OK, class, how many red flags can we see in this man’s behavior? I count about half a dozen. Honey, as a man also in his 50s, I can tell you one thing for sure: What you see is what you get. If you seek commitment, it’s time to wash that man out of your hair.

Mia: Besides all the red flags, this guy is a total old head! He’s 50, you’re 36. By the time you hit 50, you’ll be helping him put his teeth in and filling his Viagra prescription. Find yourself a guy closer to your own age who’s not so set in his ways. You deserve better.

Q: While I was in Ireland in 1997, I met a girlfriend from Ohio. The problem is I don’t see her at all. I think I need somebody closer to home. Also, what about dating services? Do they help?

Mia: It took you seven years to realize that you’d rather have a local girlfriend? Talk about slow on the uptake. First, break up with her and then start trying to meet new people. Go to parties, bars, see if your friends know any single women. As for dating services, I think they’re a little sketchy, but a good friend of mine met her boyfriend of a year through an online dating site, while I’m still single. So try both approaches. Good luck!

Steve: Location is as important in romance as it is in real estate. If you can’t move, then you need to find someone closer. I know nothing about dating services, but speed dating — where you have quick interviews with 10 potential dates to see if you click — sounds more efficient than hanging out in bars.

Q: When I turned 25, I inherited a sum of money from my grandmother. There was one stipulation: that I marry within my Jewish faith. She didn’t know I am a lesbian. Since my grandmother’s desire was for me to get married and have children, my brother thinks I should give the money back. My partner thinks I would be caving in to discrimination. I feel torn. What do you think?

Mia: She never said you had to marry a man. Can’t you just marry a Jewish chick? It’ll be legal one of these days. Mazel tov!

Steve: I hate to sound like a moralizer, but only you can decide what your grandmother would have wanted, given this new information. If she was loving and open-minded, I suspect she’d be happy to see you settle down with a nice Jewish girl.

Q: I’m an average-looking single guy in my 20s. My friends say I’m fun. But maybe only one out of every 10 women I ask out says yes. I’m so sick of rejection I hardly ask anyone out anymore. Any advice?

Steve: Be warned, Mia, sports metaphor ahead. A college buddy of mine was neither handsome nor charismatic. But he scored more than anyone I knew. His secret? He threw more passes. His completion rate was lousy, but he didn’t let rejection get him down. The lesson? The more you pass, the more you score.

Mia: I don’t get this “passing” and “completion rate” doublespeak, Steve. But here’s what I do get, Average Joe. If your main attributes are being not-totally-hideous and funny, then you need something else to attract women. That something else? Money. Lots and lots of money. There are always women who will go for a mediocre-looking millionaire. Good luck!