Happily Ever Single And Dating Multiple Guys – Can it Work?

You know the saying “When it rains, it pours”? Well I’m currently coming out of a dating tsunami. Thanks to warmer weather, my friendly nature and one Memorial Day weekend on Tinder.

Let’s Break it Down

• I’ve got a FWB* thing going on might be over with a 24-year-old guy. We met at a party where I knew no one and we ended up exchanging jokes and doing lunges in the kitchen all night. But I thought he was gay. That turned out not to be true which gave me 20/20 vision on his definite straightness and nicely sculpted 24-year-old chest, abs and arms. Apparently he liked the older woman. Yes, please and thank you.
• I’ve got date #3 planned with another man nearly 20 years older than Mr. Above – who I’m likely dragging along because there’s zero sexual chemistry, but he’s not doing anything necessarily wrong so got to give a man a chance…
• There’s the Tinder match that I wasn’t sure about that came on heavy on our first date and knows how to see right through me (I actually cried in front of him over getting a text from my dad. I know, I know, bad move but how can you not tear up when a man says, “You love your dad a lot don’t you?” when it’s a week from Father’s Day and you live out-of-state.) He’s currently in the potential fading me out zone, however, but TBD if he makes an appearance. (Update: he made an appearance after two weeks out. The delay was acceptable due to life issues, but I’m making him sweat this one out for sure.)
• There’s one that seems very, very interested and model to the fact that patience, timing, follow-up and nice dinners will get you exactly what you want with a woman. Wink. wink.
• Oh, and I have a new work crush that does everything for my lumberjack fantasy that heated cream does to chopped chocolate poured over flour-less chocolate cake. I get a feeling I may do the same for him, but I’m trying really hard not to do the proverbial shit where I eat.

Aaaand it’s finally summer in Chicago after a bust-ass winter, and we all know that’s when the boys and girls come out to play…

You wanna talk dating? Pull up a seat.

I date a ton. In fact, I’ve dated more than I’ve had serious relationships. My last real “I have a key to your place, met your mother, know how you like your steak cooked and your coffee sweetened” relationship, ended at the end of 2008. It’s 20-fucking-14, y’all. Granted I’ve had the two month-er’s in between, but anything less than six months isn’t official to me.

And even with all that dating, I’m still single. It’s not that I’m not trying, because I obviously am and it’s not like I haven’t had solid contenders, because I have.

So, what’s my problem?

The serendipity of time, commitment issues and reason #426 why I should’ve been a dude.

I’ve found my match several times since I started dating as an adult. If any of those men would’ve wanted to invest in happily ever after, homegirl would’ve said yes. Oddly, they were also the relationships that dragged me into the ground emotionally, trapping me by the idea of the man I thought they could be. Trapping me by the first kisses that took the joints out of my knees. Trapping me by a chemistry that knocked the sense out of me and had me doing stupid things that wine and liquor are known to inspire at 2:00 in the morning. They were my Notebook moments, the mornings after where unknown bruises appear and you can’t find your right shoe. And they were great. But for some reason, probably a good reason, we were not meant to be.

In the mix of all that were the John’s and Steve’s, the Mike’s and the Scott’s. All fine, take home to mama, ready and waiting to roll out a red carpet for me, kind of men. And I let them go, because while they were good candidates, they didn’t keep my attention for long. And this girl has no problem being alone. In fact, dare I say I really enjoy it.

Now, I know at some point if you do want to to this whole, settling down/family thing you have to lock up the fantasy and get realistic. I learned a long time ago that you can have a relationship of passion or you can have a relationship of care, respect and intimacy. But you can’t necessarily have both. This ain’t Hollywood.

But that’s not the only reason why I’m single.

Somewhere between last year’s breakups and this year’s dating escapades, it appears I’ve turned into a bit of a commitment-phobe. Part of it is because I don’t want to give up my freedom to date; I love dating. Another part is that I’ve been single so long, I wouldn’t know what to do with another person in the mix, and other people’s shit annoy me. But another part of it is that I’m standing on the edge of knowing that at some point, whether it’s in five years or fifteen years, I’ll probably have to move back home. Is Mr. Chicago going to want to pack up and migrate South to humidity and crazy accents? Probably not. So introducing another variable that may or may not be permanent (because in your thirties, unless you are just getting out of a divorce, you don’t date for fun) scares the shit out of me. I, like the forty year old bachelors, don’t want to give up my freedom and/or my mobility.

You want to talk comfortable, this girl is swimming in comfortable. And when you turn 32 and realize that you can attract both the 22 year olds and the 50 year olds (not that I would want to entertain that idea, but there’s skill in that), you become the CEO of “This Is My Dating World” bitches, and we need to do a little reorganization here with me on top. (You can make of that what you want.) Which is also why I recommend dating multiple guys. Note, I didn’t say sleep with multiple guys; that’s some complicated shit right there. But dating more than one person gives you a different perspective. You move slower, you make better emotional choices about a life partner, you laugh more, you eat well. You become in control of a situation that you’ve largely felt out of control for so long. You’re not crying over why he’s not calling, you’re debating if you want to call him back.

So, until I find the man who feeds both my intense/kid side that needs the bantering and the snarky yet playful fighting, my ambitious side that is looking for the Jay-Z to her Beyonce,  my calm, “womanly” side (did I just say that word?) that needs the delicacy and security of someone who is able to communicate on a mature, intellectual level, aka, me with a penis, the dating continues.

Let’s just hope I get over my geography issues before these ovaries decide to close down for business.