Advice: Born to Flirt

I have been working out, dieting hard, but not losing much weight. There’s a guy who comes in where I work and flirts with me, but he seems like one of those guys who flirts with almost anybody. I am too chicken to ask him out! Why? Well, I am quite overweight. I was also taught woman don’t ask men out, that it’s chasing, and that men who are chased run the other way.

Not everything we are taught is correct to start with, and sometimes what we learn becomes outdated as mores and customs, to say nothing of life circumstances and opportunities, change. The fact is, girls do ask guys out all the time these days, and guys often love and positively respond to the show of interest. But you don’t have to be that aggressive if it makes you uncomfortable. In fact, the possibility of rejection is always a big risk to take. However, you should do a little exploratory research first and test his true level of interest. In fact, it is a good basic problem-solving technique, a rational thing to do not just in this situation but in many others where the outcome is uncertain. It’s called testing the waters.

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Don’t ask Mr. Flirt out. Just flirt back. Keep it light; keep your own feelings a bit ambiguous. But feel free to tease him about his. “Oh you just say this to all the girls,” you might say if he pays you a compliment or interest. Or the next time you see him, look him directly in the eye so he knows you are engaging him, smile unambiguously at him, say nothing, and then shyly look away. Try that a few times and if he begins hanging around a little longer, you have a partial answer.

But a few considerations first. Your own dissatisfaction with your weight may be coloring your view of yourself—and your assessment of his interest in you. Yes, he could be a born flirt, but even born flirts don’t waste their energy on people they don’t like.

Love, Guilt and the Kids Six years ago I met a man who was in a loveless marriage; so was I. While we were both pursuing divorce, we dated for three years, living together for the last one. His children, then 13 and 16, were totally against us being together, making demands on his time whenever they could. They made him feel guilty for wanting a girlfriend. We never spent time together with his kids, and he wouldn't even talk to me on the phone when they were around. They were defiant about his staying married and staying home with them. My two kids, now 22 and 32, love him and want us to be together because they want me to be happy. I concluded my divorce but he did not.

Three years ago he found out he had cancer, had surgery, and lived with them and his (still) wife while recuperating, and for the next three years.

His daughter will graduate high school next month. He is unsure what to do, thinking his kids will hate him if he gets a divorce and moves in with me again. He feels guilty wanting to be happy because his kids say they still need him.

He is very concerned the kids will never accept me. He is afraid to stand up to them and tell them what he needs and how he feels about me.

We have just started seeing each other again, still very much in love and want to be together. How should he approach his kids and make them understand? His parents don't live together but are still married, and his sister who is unhappily married, stayed married just for the sake of the kids and told him it is his responsibility to do the same.

As you suspect, his real responsibility is to know his own mind, decide the best way to live his own life, independent of Mom and Dad’s decisions, and to assure ongoing relationships with his own children. None of those preclude happiness and remarriage.

Divorce is a reality, although one that should never be undertaken lightly. It is an admittedly painful way to end a relationship that started with great hope but has become an empty shell sustained only by guilt.

Lover Boy sounds way too comfortable with guilt. The real source of his may be striking a path divergent from the one his parents have trod themselves and deemed best for him as well. His children’s attitudes may be a convenient foil and a plausible excuse for the true source of his paralysis—continuing loyalty to his parents and sister, no matter how miserable the lives they have chosen for themselves.

In some families a shot at happiness takes a distant back seat to the grim execution of obligation, especially when it has become an entrenched family tradition. But each of us has the obligation to decide which family traditions work in our own lives and which do not. That’s called growing up.

Children rarely ever welcome the breakup of their parents’ marriage. And even far less often do they open their arms to a potential stepparent, at least at first. Children are likely to regard a stepparent as an unwelcome interloper into the family they already have, or as a competitor for a parent’s attention, or sometimes even hold them responsible for the breakup of their world.

But it is not a child’s place to make certain decisions. And giving children that influence and power is not good either for children or parents. It puts children in the driver’s seat and becomes a source of anxiety, because at some level they know they are unprepared to run things.

Lover Boy need not abandon his responsibility as a father to choose a future for himself that involves love. In fact, he needs to make up his own mind where his best interest lie, and if they are with you, he needs to tell that to his children while assuring them he still loves them and expects to continue the relationship with them.

It is unrealistic for either of you to expect instant rapport between you and his kids. Trust takes a very long time to build. But they will never waver in their respect for their father if he pursues a life charted not by his parents’ values but his own needs and values.

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