Advice: Born to Flirt

He flirts with me, but I'm too chicken to ask him out.

By Hara Estroff Marano, published on May 1, 2004 - last reviewed on January 23, 2015

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sometimes what we learn becomes outdated as mores and customs, to say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.

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.