Urban Thought Collective

Okay, once again I’m asking ya’ll to take a little ride with me, but first check your judgment at the door until you’ve heard me out.

I consider myself to be a good Christian girl. Not a perfect one, and by some strict, conservative standards maybe not all that Christian, but we’ll save that for another time.

Most would describe me as forthright, loyal, trustworthy. I once returned a set of designer storage boxes after realizing the sales girl forgot to charge me for the three boxes tucked inside the fourth larger one. Notice the use of the word once. There was another time when a certain Calvin Klein tuxedo pantsuit was rung up using only the jacket tag and I kept mum. Sadly, this tuxedo marked the beginning of the end of a year long relationship when I decided to wear it to my good friend’s second wedding and my boyfriend insisted I wear a dress. We broke up the next day. Hark! I hear some judgment coming on. Let me add, the tuxedo argument was a symptom of a bigger problem. I didn’t really dump dude because of it, okay? The point I’m trying to make here is that I believe in karma that maybe, me and my ill-gotten tuxedo had it coming.

Enter my dilemma. This past weekend I went to this shi-shi little Hollywood party. I was dateless but meeting up with a gang of friends, so it was all good. It was one of those nights where the stars must have been in perfect alignment because me and my little black dress were killing it. My hair was big and fluffy (intentional), my make up was flawless (I went the less is more route to match my dress) and since I’d put in a little extra time in at the gym, I was partying Spanx free.

I didn’t notice him at first, I hadn’t seen the boy in years, but I did notice his date, pretty girl. We run in the same circle and therefore we’re friendly but not friends. I mention this now because it will become important later. She was looking good too and so it was in the middle of me complimenting her dress that I finally realized I knew him. We hugged hello, no reason not to. We’d hung out a few times back in the day, shared some laughs (dude is quite funny), but no romance, and definitely no drama.

Cut to the party’s last legs, just a few hard core revelers hanging on. My three-inch Gucci quilted platforms were giving me the blues so I was chilling on the couch like I owned the place. He and she join me, as her dogs were starting to bark too. Soon we’re surrounded by folks taking a reprieve from the chilly Cali night air or looking to find a comfy sit down. Within minutes she’s chatting it up with someone and he starts chatting it up with me. We played catch up. His son just started college, I’m now writing (as opposed to producing). He just bought a house in the hills, I’m now living at the beach. Blah, blah, blah. We exchanged contact info, promised to do lunch, and I headed outside to smoke my first Montecristo White Especial Cigar. Smooth as butter, baby, just FYI.

A few nights later, he rings me up. He shoots me a compliment about how good I was looking that night, I shoot one back. He’s held up pretty well under the years. Not all brothas do, you know? Some of you guys out there could use a pair of Spanx your damn selves, but I’ll save that for another time.

We play catch up once again. He’s working on this project, I’m working on that project. He’s feeling the Giants this season, I’m rooting for the Eagles. Blah, blah, blam! He oh so casually drops in that he met ole girl on the internet and that they’ve only been out two times. A “she’s not my girlfriend” disclaimer if I ever heard one.

Now ya’ll know where this is going…the boy asked me out, only it more like a “save the date.” Yes, you heard me. Homeboy was on his way out of town for two weeks (his mother’s having hip replacement surgery in Ohio) and upon his return he wants to take me to dinner. How cute is that? Both the going to Ohio to take care of his ailing mother and the I want to take you out two week notice thing. I’m a sucker for the care-giving, organized type what can I say?

Except that I’m not so much a fan of the get the number of date #2 while out with date #1 type. I’m not stupid. Who’s to say that while out on our dinner date, homeboy doesn’t pull the digits of chick #3?

I’m also not a fan of the going after another girl’s guy type, which technically I’m not, because dude came after me and he made a point of letting me know how much of a couple they weren’t, but I still can’t help feeling a little guilty about it. I mean, regardless of their official relationship status, she did look like she was into him.

If she and I were friends, I wouldn’t even consider it, but as I said, we’re not. I don’t have her phone number, email address, and we’ve never broken bread. I’ve been in the game long enough that almost every guy I meet has dated some woman I know. In my younger days, this would’ve been enough for me to back off, foolishly believing there were plenty of fish in the sea. But one thing age has taught me, throwbacks don’t count, okay? The sea is full of scrawny, sickly, slow swimmers. Catches of the day are hard to come by (same goes for female fish, so calm yourselves down guys).

The other thing age has taught me is that there is no perfect way to meet somebody or re-meet somebody as it were. Waiting on perfect, has me going to shi shi parties alone. Yes, I wish homeboy was not on a date when we re-connected, but he was only there as her plus one. If he weren’t there on a date, he wouldn’t have been there at all. Yes, I know I’m rationalizing and for those of you who think for two seconds that if dude were married or in a committed relationship that I’d still be rationalizing, you’ve obviously learned nothing from these last few months we’ve spent together nor are you trying to, so stop reading and don’t bother weighing in.

So there you have it, my dilemma in a nutshell. I’m just a good girl, out here trying to do the right thing. Do I or don’t I go out with dude? Ready, set, judge!

Tamara T. Gregory is a writer/producer/traveler. Happily single (yes, there really is such a thing), she is an expert on the dating game. Her debut novel, Passport Diaries, is an LA Times bestseller and is soon to become a Hollywood motion picture. The book is available at www.passportdiaries.com. Gregory’s X…WHY blog is exclusive to Urban Thought Collective.