I Go On A Lot of Inadvertent Dates with Women

“You’re a natural flirt.”

This was first said to me by my first serious girlfriend. And then my most serious girlfriend (we’re going to call her, ‘S.K.’) said it. Then my boss said it. Friends of both genders have said it. And my response has always been, “Nonsense! Baloney! Poppycock!”

Until tonight.

So about tonight, I was invited out to a comedy club by a friend who just happens to a woman. I’ve known her for awhile as we sometimes cross paths because we both do a lot of work in the same industry. As I think about it now, doing the uncomplicated math in my head, it has been approximately 2.5742 years since I have known my friend, ‘Lime’ (I have decided, spontaneously in this moment, that Lime will be her name for the rest of this post). Recently, Lime and I have been corresponding more and more often. We’ve sent a few emails back and forth and texted a couple of times a week, just shooting the electronic breeze. We even hung out once. So, I’m thinking, “cool, I kind of like Lime, she’s pretty cool and she’s into hip hop, which earns her mad points, like she hit the bonus round on my pinball machine…we can be good friends.” Notice the italics. Basically, I’m thinking all of our interactions at this point are innocent and strictly platonic, and you know, looking back on it, perhaps they were.

But tonight makes me think differently.

For about half a week Lime has been texting me about various things happening in the city, including this comedy night that happens every Monday at this club that I happen to like, where my friend’s band has played before and where I recently attended a hip hop jam that has made my Top 10 All Time Greatest Parties list–and I’ve been to a lot of parties. Basically, Lime had me at, ‘hello.’ So, when Lime suggested we hit up this spot (that I loved) for a comedy night, I was very firmly and decidedly doooown!

We made plans–we were hitting up the comedy spot on Monday night.

But, as things go in Toronto, situations come up, plans change, and communication is frayed as us young, ambitious, (and beautiful) city folk are sometimes too busy and disorganized for our own good. Or maybe that’s just me. Either way, our plans fell through.


How did our plans fell through? I was supposed to text Lime to confirm, and I did, but I guess I texted too late so she went for a run and I played some basketball. So late in the evening, Lime and I caught up with each other and we decided to hit up the comedy spot, albeit late. As such, I went to pick up Lime and she hopped in Scarlett II (my car–not to be confused with my Grade 6 crush, also named Scarlett). We decided, because I was starving after having dominated on the basketball court like Lebron James on steroids only minutes earlier (I may be exaggerating), I felt I deserved a meal. After all, I did finish one of the games like this:

Complete with the eye-of-the-Tiger glare and the walk off. It was a good moment.

Anyway, due to my excessive hunger derived from the sweet sap of greatness and triumph, Lime, who had already eaten dinner, suggested we hit up a gourmet pizza spot whose pizzas literally received a stamp of approval from Naples in Italy. At this point I’m thinking, “yup, this pizza has got to be LEGIT!”

So, I drive Lime and I to the pizza spot. We sit down, order pizza and eat (the pizza was indeed exceedingly legitimate). As we’re at the table eating this amazing pizza, talking and joking around, I start noticing that Lime is laughing at a lot of my jokes. And not just laughing, but laaaaughing. And, while I’m a fairly entertaining guy if I do say so myself, well, I’m not that funny. But, Lime was laughing at my jokes like she was out with Dave Chappelle and not Asante Haughton. This is where I start to clue in, thinking to myself, “uh oh…am I on a date…and is Lime starting to like me?” But again, “Nonsense! Baloney! Poppycock!”

Or maybe not.

Because later that night, after we had left the restaurant with the gourmet pizza (which deserved not only a stamp of approval from Naples but also from God), I drove Lime back to her apartment and then this happened:

Me: “Okaaaaay, so we’re here.”

Lime: “We are. Thanks Asante for driving me home.”

Me: *Smilingly*  “No problem. Anytime.”

Lime: “And thanks for everything else tonight, it was all really sweet of you.”

Me: *Thinkingly*  ‘oh snap, did she just call me sweet?!’ and I finally reply, “…ummm…thanks, uh, not a problem…at all.”

Lime: *Looks down, then up at me, then down again, as if waiting for something.*

Me: *Looks at Lime, then looks past her through the passenger-side window.*

Inside the Car: SILENCE.

Lime: *Continues to look down and then at me, again, as if waiting for something.*

Me: Trying to break the awkwardness, I say, “so, um, uh, it’s getting late, what’s the plan?”

Lime: “Oh, uh…yeah, you’re right, it is pretty late…”

Me: “Yup!!”

Lime: “Yeah, I guess I’ll go upstairs now.”

Me: “Okay, sounds good.”

Lime: *Waits some more.*

Me: “Well, I gotta get some sleep. Thanks for inviting me out tonight.”

Lime: Presumably now done waiting, exclaims, “Okay, bye!” as she exits the vehicle.

Me: *Watches Lime enter her apartment building before driving away thinking, ‘well that was a little weird…why was she taking so long to get out of the car…like, what was she waiting for?’

And then I drove home.

This is why I’m still single.

It occurred to me, pretty much as soon as I put Scarlett II in gear, that in the car after dinner and in front of her apartment, Lime was most likely waiting for a kiss, or for me to at least make some kind of move. And I completely missed all of the signals! I didn’t even catch one of them, like a football player who didn’t read the playbook. *Whoosh!* It all went way over my head. Then I started getting flashbacks.

This was not the first time this situation had happened to me.

This scene–of me dropping off a young woman at the end of the night, with the awkward goodbye, the waiting, the longing looks, and then the looks of disappointment that scream, “dammit boy, why don’t you just kiss me!”–has happened quite a lot. More than I’d like to admit. It happened with Orange, and with Clementine, and with Tangerine, and with Lemon (though it wouldn’t have worked with her anyway, her attitude was too sour), and countless other women that I won’t name because, well, I don’t know the names of any more citrus fruits. The point is, this situation, where I have seemingly gone on what I thought to be a platonic outing with a friend of the opposite sex, has happened quite often in my life.

It appears that I’m completely oblivious to the signals that women give when they like a guy. It’s a wonder I’ve ever even had a girlfriend at all–or so many of them. Even my most serious girlfriend, S.K., whom I referred to at the very beginning of this post, well, her and I first went out as what I thought was platonic friends. Then after we had seen Zombieland, the film of choice that night, we headed back to S.K.’s crib after the movie to play video games. Hours later, we’re still playing video games and it’s too late for me to get home comfortably on public transit and I’m too far from home to call a cab (I didn’t drive at the time), so S.K. invites me to stay over for the night. I say, “cool, I’ma just hold down the couch right here.”

Which is what I did.

I woke up the next morning on the couch and went home. About a week later, S.K. and I hung out again, and a similar scenario transpired (we hung out, then she invited me back to her place for video games), except this time, she ripped the Wii-mote out of my hands, grabbed me and started making out with me. And the whole time as this was going down, I was thinking, ‘well, this is a surprise…but I’ll go with it!” as I was completely oblivious that she was even interested in me romantically at that point.

Completely. Oblivious.

S.K. and I ended up dating for quite awhile, and even lived together for over a year. It was all a very beautiful experience. And once, during our relationship, we reminisced about that Zombieland date (which I didn’t even know was a date), and she explained to me how frustrated she was with me that night as she expected me to make a serious move on her, because, really, as she said, “what woman invites a guy to stay overnight if she isn’t interested???” And I shrugged and mumbled, “…um…I dunno…” However, in my defense, I will say that six weeks before Zombieland with S.K., I had just broken up with a girl whom I was deeply in love with that cheated on me. I was still heartbroken, stuck in that damp and dark pit of low self esteem that happens after being cheated on, and certainly not looking to hook up with, sleep with, kiss, make out with, date, or be in a relationship with anybody at that point. After all, I was too busy writing sad poetry and listlessly watching the Toronto Raptors lose basketball games while listening to songs about depression by Joe Budden (his tape, Mood Muzik 2, is a terrific project in this regard).

With all this being said, yeah, I was completely oblivious to S.K.’s interest in me (because texting me throughout the day everyday, talking to me at night every night, and inviting me to stay overnight after a movie doesn’t mean a woman likes you at all in my head, it just means she’s a nice person). And yeah, I may have gone out with a lot of female friends and acquaintances over the years who, like Lime, invited me out and then waited awkwardly for me to make a move at the end of the night. And then many times I haven’t. Because I didn’t think I was on a date. When in fact I was. And tonight, it really hit home for me that I’m very often completely oblivious to women’s signals of romantic interest, that I probably unknowingly have led a lot of women on, and that this must have been incredibly frustrating for them.

Tonight I realized that I go on a lot of inadvertent dates with women.

No wonder I’m still single.

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