Advice to a Middle-Aged Woman Re-entering the Dating Pool

It's titled "Jumping Back In" but is there still water in the pool? "Bella" wrote in to Dear Margo:

After a marriage of 20-some years, I am about to dive into the middle-aged dating pool.

Oh boy, is she in for some fun.

I suspect it will be very different the second time around, but part of me thinks it may be just like picking up where I left off.

The first one is right for two reasons: 1) the rules have changed, and 2) you've spent up one of a woman's most valuable dating assets - your youth.

Friends tell me, however, that it’s a whole new ballgame and difficult.

Yup!

Dear Mago metions baggage, then ends with:

But … chins up. The men you will be seeing are just as nervous as you are, and I’m here to tell you that you will get the hang of it.

Dear Margo is either oblivious, delusional, or didn't have the heart to tell this woman the truth. Some of the people commenting did, though.

There are two big questions that the letter writer should have answered by including the information:

1) What are you looking for in general? Free dinners and entertainment? Another marriage? Steady companionship? Sex? If she's getting alimony, she may not want to get remarried if she values the steady money over marriage.

2) Are you willing to try men significantly younger or older than you?

Almost all of the successful, desirable, dating heterosexual men around near her age are divorced or on a marriage strike and dating younger women. If she wants to marry or even date a man near her age, she's probably going to have to be open to dating men who can't afford to pay for her to have nice dinners and entertainment, never mind financially support her if they marry. If she wants those things, she will almost certainly have to go with a significantly older man. If she just wants companionship and doesn't care if the guy is "of modest means", then it isn't so much of a problem.

She'll also find it isn't a problem to get sex if that is all she wants, but it will be easiest to to be on the "A" list with guys who are younger (since women their age are dating older men) or significantly older. Guys around her age will probably have her on the "B" list.

Speaking of sex... there's no short supply of younger, hotter women than her willing to have casual sex with the men she'll want to date. Most men these days expect it by the third date, if not before, and a lot of women consider themselves rejected if he doesn't try for it by then (if those women aren't taking the initiative themselves).

Those are the brutal, harsh realities.

If she wants to marry a successful man near her age who would make a good husband, her best hope is going to be to find a divorced man whose wife threw away a perfectly good husband, yet he hasn't been turned off to marriage. If he has no minor children, that will be the best scenario. He'll likely be paying alimony to his ex-wife, though. (If he was widowed, she won't have an ex to deal with it all.) To snag such a man, she's going to have to compete against those younger women I wrote about above. The does not mean she has to jump into bed with him – if he thinks sex is for marriage or only for steady, exclusive relationships, he'll appreciate it if she keeps that boundary in place. She should play up her advantages over those younger women (if she has them) – a better understanding of how to keep a man happy (did she learn from her ended marriage?), better earning ability, more experience in social graces, etc.

Enjoy!

Sheesh... after I wrote all of this I remembered having written something like this before. Previously:

A Question for the Ages

An Unmarried Woman

She Might Have to Go Older or Younger

Is It OK For Her to Ask For a Date?