Is It OK to Date More Than One Person at a Time?

by Rich Santos/ marieclaire.com

Despite knowing I should play the field more, I haven't been able to bring myself to do it.

I was recently hanging out with a girl named Pam. I could tell I liked her because I got into a good mood whenever she texted/talked to me.

While I was hanging out with Pam, I went to a party and met a friend of a friend named Nicole. The next day, I found out that Nicole thought I was cute, and I was faced with a quandary...because Nicole was cute too.

To make matters worse, they were complete opposites: Pam was younger, just starting off in the work force, and Nicole was a bit older and she was a lawyer.

So all of my guy friends and even most of my girl friends were telling me to hang out with both women. Essentially they advised me to "see other people."

I've never been comfortable with the idea of "seeing other people."

Here are pros and cons of seeing other people:

CONS

I Feel Guilty

Would Girl #2 be hurt knowing I was out with Girl #1, or vice versa? I'd debate this in my head while out on dates with one of them.

I'm A Bad Multitasker

Incomplete projects strewn around is a hallmark of the ADD-afflicted person's life. I've got plenty of those. Considering I have trouble following through with one girl, how much trouble will I have following through and managing two different relationships? And, let's face it, I'm not used to more than one girl liking me at a time.

I'm able to manage multiple friendships, because it's important to me, so maybe if relationships are important enough, I can pull it off.

I Might Lose Both Chances

The biggest element of my quandary is deciding whether I should tell both girls about the fact that I want to see other people. If I do, it might work out better, but I could lose them both if they don't like the arrangement or if they find out if I tried to keep it from them. If I tell both women, I'm officially seeing other people. If I don't tell them, does that mean I'm two-timing?

I'm Not Guy-Like When It Comes To Sex

I think most guys would like the opportunity to be with two women. Quantity is ok, but I've never been seriously sexual with two women at the same time. In fact I've never had sex with two different women within at least 3 months. If I ever did, I'd feel overwhelmed and a bit dirty in a way (growing up Catholic messed me up).

It Could Get Overwhelming

I'm a bad time budgeter, even when I'm not dating. Dating two women could create a time issue, although my buddy told me to look at it as a reward for working hard during the day. He told me to cherish the time I spend with women-and I can do that, I've recently re-discovered how nice it is to have a female care about me.

But what if one or both of these relationships gets serious? If one gets serious, then I have to hurt the other girl by cutting that relationship off. If both get serious then I've got a problem on my hands.

PROS

Keeps My Options Open

Seeing other people obviously allows me to take advantage of any opportunity I have.

Provides Benchmarks

So, do I want a younger girl, or an established lawyer type? The only way I can figure out the type of girl I want is by dating as many as I can.

I Might Lose Both Chances (Reprise)

Is dating a numbers game? Great relationships don't come along too often, so taking as many chances as possible ensures a higher chance of something working out.

It Will Give Me Confidence

I guess you have to be selfish in dating sometimes, and who doesn't get more confident when a few people are into them?

I'm Probably Not The Only Guy

Who am I to think that these women are not playing the field as well? I guess all's fair in love (and war-same thing). How stupid would I feel if I didn't play the field and later found out that one or both of these girls was seeing other guys too?

What are your thoughts on seeing other people? Do you think it's a fair thing to do, or do you think it's risky/dangerous? Do you agree with my pros and cons above? Should I tell the women I'm seeing other people or keep it secret? Is it two-timing if I don't tell them both the truth?