Answers To Your Questions About Dating At 50+


Three-date rule?

For mature  singles (60+), is there such a thing as the three-date rule? In other words, if there is no intimacy by the third date, there’s never going to be any so, move on? — Sheldon M., 60, Los Angeles

Sheldon, I’ve written more than 800 newspaper columns on dating at 50+ and I can assure you, there is no three-date rule. Most women want to know a man before becoming intimate with him. That often takes many more dates than three. If you find a woman you like and she wants to wait, you’d be a wise man to honor her wishes. Plus, you’d know that she’s particular with whom she is intimate. Be a gentleman. Good partners are worth the wait.

Ultimatum or wait for him?

I have been seeing/dating a man for almost one and a half years. We have a monogamous relationship however he’s continuing to keep his profile online. He has not shown any signs of our relationship being anymore than what it is currently, although when asked he says he is not interested in ending what we have now. I would like to take the next step with more of a commitment, but am afraid of jeopardizing what we currently have. I don’t know if I should approach him with this on a more serious level. — Carol W., 53, Cave Creek, Ariz.

Carol, sounds like he’s content with the status quo and likely enjoys the sex, but he has no intention of taking the relationship to the next level. Plus, if he’s still online, he’s also looking. So you need to decide what’s more important to you: Continuing the way it is, even though there’s no guarantee he won’t meet someone else; or, giving him an ultimatum that you want more out of the relationship. That’s totally up to you. However, if you choose the latter, realize that he might end the relationship and then you’d be alone.

Settle for insecurity?

I’ve been seeing a guy for a month now. We emailed each other for a month before that. We are both 50 and single. When we are together it’s great. However we never set up a definite next date. For him it’s always wait and see. That leaves me feeling insecure about the relationship. He says I am the only one he is seeing romantically. I come from a very bad marriage that left me very insecure. I feel very comfortable and wanted when I am with him but it goes away when I have no contact with him. Should I just try to get used to this? — Valerie R., 50, Dowagiac, Mich.

Valerie, are you asking, should you “settle” for insecurity? That’s up to you. You can continue to see him based on when he feels like it, but if I were you, I’d develop other friends and relationships to cover your bet. Keep an eye out for someone who would appreciate you and would make you feel secure. People deserve to be with people who care about them. He’s kind of dangling you on a string, and you’re allowing it.

A little married?

I have gotten a few Icebreakers from men who have classified themselves as being “separated.” According to the law, they are considered still legally married. If I do accept a casual date from a man who is separated, isn’t that considered going out with a married man? — Judith H., 57, Hicksville, N.Y.

Judith, well, yes, you’re going out with a married man. But, don’t judge all people who are married but separated as being wrong to date. Some are just awaiting their divorces, others haven’t divorced because of children or financial considerations. You might meet someone wonderful who is separated. But it’s risky. How do you know who’s being honest with you vs. the married guy who wants an extra-marital affair? That’s where the problem lies. Just be careful, but don’t automatically eliminate a separated guy.

Age denial?

I find that men my age are not really looking for women their age, no matter what they insist to the contrary. Of course, I could be 85 as long as I look 35, but that’s beside the point. Why are so many men in denial about their age? No matter what their physical condition, they want women who are beautiful. — Marte T., 55, Cupertino, Calif.

Marte, what they want and what they can realistically have are different issues. If all a man wants is a younger, beautiful woman, avoid him. Why are men in such denial? Because they don’t know any better and have over-inflated opinions of themselves. Many, in due time, come to their senses and pursue women closer to their age. And they end up happier.

Dressing distress

Are dress standards for men meeting a woman for first time are now ultra casual? Most of the men I have met put little effort in their appearance for a first meeting. Some need haircuts and beards trimmed along with showing up in blue jeans and gym shoes or shorts and well-worn shirts. I do put a lot of time and effort to look especially nice for them. I don’t understand why men do not feel they need to present a good image as well. — Judy S., 56, Newport, Ore.

Judy, I don’t understand it either. Well scrubbed, clean clothes, trimmed hair and clean fingernails are what make a good first impression. If a man has the appearance of a slob on the first date, guess what, it isn’t going to get any better. Don’t completely write them off, perhaps with some simple coaxing and suggesting a guy might get the point. However, I agree, first impressions are important and if a guy doesn’t care about them, chances are he’s not for you.