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Lately I've been jumping from guy to guy or date to date with quite a bit of ease of mind. It's unusual for me, especially considering how I used to focus on guys with an almost religious fervor.

Most of the reaction I get from friends is "Good for you!" or "That's what you should be doing!" But another friend of mine, never married, in his 40s is also dating around -- three women to be exact. On one Saturday, he went out with all three of them at different times. They don't know about each other. Those same friends of mine don't receive his story nearly as well as mine.

So my question is this: At what point is dating around good and healthy and when is it a crime?

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Comments (11)

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Ruby said:

If nobody thinks you're exclusive, what's the big deal? That's why it's dating, not engagement, right?

But three dates in the same day seems brash to me. Is he so irresistible that each woman would have died if he had said no to her for that day, or is he just showing off? That's the only part of that that bugs me.

But maybe I'm judging because of the number. I know I have had dinner with one date then gone out afterward with another. It's just a small difference between two and three, I guess.

Betty said:

Yeah, I think the problem when one person prematurely assumes exclusivity.

As far as the guy with three dates in one day, he's probably showing off. But why not? I certainly don't have that kind of dating stamina!

Wingfella said:

At a party the other night, I told a friend that I just didn't have it in me to go pick up women. Takes more energy than I cared to spend that particular evening.

I have no idea how your 40-year-old friend does it. Just one date in three days seems like a lot to ask. Three in a day doesn't seem impossible or wrong, just really taxing. And if you're dating/single/not exclusive, then what's the big deal?

If you're a decent person and aboveboard about yourself and your actions, then it should be OK.

Betty said:

No kidding. He took one woman to breakfast, one to a mid-afternoon sporting event, and the third to dinner. That's an intense day, dating or not.

xxx said:

um, did he pay for all those dates? if, so let a playa play

Ruby said:

And expensive.

Chronicles of the wingman said:

at 40...hmm..it could've been: he took his mother to breakfast, his daughter to a sporting event and gone out on a real date that night. I know some older guys that pull that trick to make themselves seem bigger than they really are.

Reggie said:

To answer your initial question – "At what point is dating around good and healthy and when is it a crime?" – it would be different with each person, wouldn't it?

I know people who, like your friend, are OK with going on 3 dates in one day. I also know people who are uncomfortable even with the idea of "dating around," either because they're shy or because they think our society is too cavalier with the idea of see-'em, leave-'em. And I know lots of people in between.

You have to do what works for you. Don't let people on either side of the equation argue you down.

Betty said:

That's all good and diplomatic, Reggie, but what if you feel one way about "dating around" and your dates feel a different way? Would it be my friend's fault if any of his three dates have some unrealistic expectation of monogamy? Is your dating philosophy something that you need to be really up front about? I know it's not something I really like to broach on a first, second, third date.

Reggie said:

Betty-

Nah. I'm for full disclosure of many things that will prevent any serious unpleasantness; letting people know that you're taken, for example. But differences in dating philosophies are just like differences in personality -- you'll find out about them soon enough, and if they're a big deal, things end quickly with no harm done.

Jizelle said:

I don't see any harm in testing the waters, because there are a lot of fish in the sea. I agree with Ruby. I think it only becomes a "crime" when the guy or gal you're dating thinks he or she is in a committed relationship....if the terms are clear, then, hey, roll with it!

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