Philadelphia Freedom

The Lesbian Woman’s Perspective: Jody Fischer

I see some assumptions floating around in your query. Are all women looking to get married? Are dates always fun? Are the only women worth dating the ones who want to be in a serious relationship?

Truth be told, as we get older, most folks look to settle down, or resettle down. However, don’t assume this is the case for every middle-aged hottie you see. And while we’re examining assumptions, what’s your idea of a “fun” date? Does that mean telling a woman you’re interested in a more-serious relationship so you can sleep with her, or is it more of a mutual no-strings-attached romp?  I’d imagine that it would probably be more fun for you if you were up front with a woman on the first date. Tell her you’re not looking to settle down now and (notice I said “and,” not “but”) would be interested in casually dating. If that simple truth cuts down on your dating-pool options, so be it. But take comfort in the fact that if you’re honest and up front with women, I won’t think you’re an asshole, either.

The Straight Man’s Perspective: Chris Kennedy

To quote Billy Joel’s 1978 hit song “Honesty”:

Honesty is such a lonely word.
Everyone is so untrue.
Honesty is hardly ever heard.
And mostly what I need from you.

Thanks, Billy. Got that, SS?

There’s nothing to be ashamed of if you want your freedom and your fun. Why settle down again if you don’t want to? You’re a grown man. I’m with you all the way, brother. Your only responsibility is to be honest about this with yourself and with the women whom you date.  Why would you date women who are looking to get married, anyway? Too much pretending to be what you’re not; be yourself.

Despite what you say, I don’t agree that you must rule out a huge chunk of women because of what you want, or rather, what you don’t want. There are still plenty of women who want to have a good time with a good guy. A good guy, when everyone is so untrue, who gives them mostly what they need from you … honesty.

The Gay Man’s Perspective: Darren Maddox

No, you’re not an asshole. Guys have been using the “I just don’t want to get serious with anyone right now” breakup line since Moses was a baby. You’re just being openly honest with your friends and family, and they’re trying to call you on your shit.

Here’s the deal: you can survive the dating world for years by telling women that you don’t want to get serious. Then you’ll move on to another woman. And another, and even another, if you’re lucky. But at some point, you’ll likely find someone you can’t quite walk away from, and then you’ll be hard-pressed to keep up the same dating trend you’ve set for yourself.  Now, with that said, not all women are created equally. There is many a good gal out there. Make sure that you aren’t using the ex-wife as your benchmark and turning against relationships as a result of your time with her. If you do feel that way, go see a professional.

My best advice to you, as you roam the streets of Philadelphia, is to be as up front as possible with the women you go out with so feelings are spared. And wear protection!

The Straight Woman’s Perspective: Rebecca Brown

Are you an asshole for knowing what you want and being honest about it? Absolutely not. You would be an asshole if you strung along women who were looking for a serious, committed relationship and you didn’t tell them where you stood, but it doesn’t sound like you’re doing that. (That would be akin to “shoplifting the pootie,” as Rod Tidwell astutely points out to Jerry Maguire in the movie Jerry Maguire. Don’t do that.)

Believe me, there are plenty of women who aspire to get married and also enjoy a little attachment-free fun every now and then. (See: The Bachelor Pad.) Tell your friends and family to step off and stop forcing their agenda on you. As Austin Powers might say (yes, three pop-culture references in one answer), marriage isn’t everyone’s bag, baby.