How to Win the Midlife Dating Game

Midlife dating can be confusing. Don’t worry, you can figure it out with a time, information and practice.

First you have to understand the matrix: Some people are after romance only; others are after marriage.

If you’re a woman dating again at midlife, you’ll find there are some men who are inveterate “husbands.” Generally they were long-married and often widowers. They want marriage again and they know it.

There are other men and women who want to have a romantic affair, possibly long-term, but not involving marriage. Take for instance the woman who is just out of a long unhappy marriage to a man who ignored her. Her immediate goal may be simply to reclaim attention from men with quantity more important than quality.

I’m eliminating here the category of “players.” If you want relationship and are confronted with a player, you can pick up on it quickly if you aren’t naïve. If it looks like a wolf, smells like a wolf, and acts like a wolf, and there’s a tail sticking out from under the nightie, IT’S A WOLF!

Another variable in the equation is the individual fit. You both may want marriage, but either of you may decide the other isn’t the candidate. You may be a perfect fit, but she wants marriage and you don’t. It’s (1) what do you want and (2) with whom?

It’s confusing and frustrating, but everyone’s in the same boat so don’t take it out on the others. It would be easier if we could all wear signs on our backs announcing our intentions, but then we’d still be left with the individual fit.

It would be even easier if all of us knew our intentions, which brings up a final category: The Good But Confused. They smear all over the matrix. You can’t pick up on them as quickly as you can The Wolf, and they sure can cause you pain. These are good folks too hurt or too new to the dating game to know what they’re doing. Beware. You don’t ever want to be someone else’s first. Let them cut their teeth on someone else. In this case the bite is worse than the bark.

They reek ambivalence and bombard you with confusing signals. They flirt, then run. If they start to get emotionally involved, they crater. If you try to talk about it, they can’t. Note: If you can’t figure out what’s going on, no one could, so give up and get out. Don’t try to fix it; it’s a blackhole.

Early warning signals can save you some time. We’ll go through some confusing scenarios.

SHE WANTS MARRIAGE, HE ONLY THINKS HE DOES

Living miles apart, Beverly met Dan on the Internet. He was ending a short marriage he’d entered into late in life. The courtship proceeded with more romance than Beverly could’ve dreamed of. Eventually Dan came to see her. Though Beverly was crazy about him, and they got along well, he left with promises that never materialized, continuing to communicate, but ambivalently. Beverly hung on for months, but it never happened.

One clue Beverly missed is there’s some reason why a man doesn’t marry until his late 40s and it’s not a good sign when the marriage then implodes. However, there’s no way to know when someone’s ready to move ahead. Beverly thought it was worth pursuing, and we’re glad she did.

When the man isn’t forthcoming with the next invitation, it’s a bad sign. Had Dan invited Beverly next to come visit him, it would’ve meant marital ideas. When the person brings you publicly into their world of friends, family and work, it signals more serious intent.

It hurts to guess wrong, but you’ll recover as long as you don’t take it personally.

HE WANTS MARRIAGE WITH HER, SHE WANTS MARRIAGE BUT NOT WITH HIM

Al, a widower, doesn’t know how to live unmarried and dates with the intent of finding a new wife. Anna was thrilled to find a playmate for tennis and dancing. The first time they played tennis, Al invited her back to his house for a drink. They ran into friends of his at the sports club, and Al always introduced her, saying, “They’re old friends. We’ll have to do some things with them.”

This is a sad situation because Anna liked Al a lot, but there wasn’t a connection there for marriage. His dating style revealed him to be a good candidate for marriage, and Anna could only feel, as you will too, “What a shame this isn’t a fit.”

TOM IS ‘GOOD BUT CONFUSED’

Tom, newly divorced, kept flirting with Nancy at parties. He even asked for her phone number, which she gladly gave as she liked him, but he never called.

Deciding to move on it, the next time she ran into him, Nancy pulled him aside for a conversation. Tom quickly began talking about his broken heart, eventually admitting he wasn’t ready to date.

Both parties learned important things. Tom liked Nancy but knew he had nothing to offer at the time, and the conversation allowed him to quit doing what he was doing, which wasn’t serving anyone’s interests. (Someone like Tom can benefit from coaching or therapy. Nancy was wise not to try and do this herself.)

REWINDING

When you realize it isn’t going to work out, you face everyone’s least favorite situation: ending it without hurting feelings.

Pros get used to the ins and outs of it, but if you’re new, it will hit you hard. After all, you’re lonely, you’re looking, you have feelings, and you know others do too. It takes finesse. You may move in the same circles, or have been introduced by a joint acquaintance.

The key is to remember that you don’t do anyone a favor by “pitying” them, using them to temporarily fill a void, or by projecting too much of your own feelings on another. When you know it’s not there for you, it’s kinder to exit gracefully and free them to get on with it.

With experience, you’ll get quicker at assessing your own feelings and the potential of the relationship, and better at the gracious exit. Just remember, there’s nothing compassionate about a lie. Everyone deserves someone who truly loves them.

If you’re after a caring romance but not marriage, and find a suitable candidate, monitor it closely. One of you may fall in love while the other one doesn’t. You need to be able to pull out of this when necessary to save your heart, or hers.

Generally speaking, men are more capable of sex without emotion. Stay alert. If you start going under water and he isn’t, throw yourself an inner tube. Not that you won’t survive, but why put yourself through it?

You needn’t be responsible for the other’s feelings, but when you’ve reached a decision-point, talk it out and do the right thing. You’ll feel better about yourself and help everyone else who’s in the game.

If you’re honest and decent about it, you’ll build good dating self-esteem. The actual relationship may not work out, but you’ll both be fine and go on to look for, and eventually get, what you really want.