50 Shades of Awkward - A First Date Story

I recently decided to put myself back in the dating game, which is horrifying when you are as close to 40 as I am. Nonetheless, I am allergic to cats, so becoming a crazy cat lady is right out for me. I proceeded to do what people do in 2017 and sign up for an online dating app without much hope. To my surprise, the guys in my area have really low standards, and I get a lot of matches right away. Honestly, all the attention was overwhelming, like walking through a room of dogs holding a treat bag. I chose one guy I particularly fancied and gave him my number.

For the sake of privacy, let's call this gentleman Sterling. While not his actual name or even close, it's suave and sexy, and it makes you want to sigh every time you say it, and this guy had one of those names. Sterling proceeded to call me as he said he would. Of course, I had forgotten he was calling and made plans with friends, so he texted me, indicating who he was and that I could call him back anytime. Now, because I am me, I leave my phone at my friend's house who lives FORTY miles away, but I have plans with her in a few days, so I just go without. Once I get it back, I have close to 1.2 million calls to return, and his slipped through the cracks, but he took it in stride and called the next day, and we finally spoke.

The conversation went well. We talked about similar interests and got a basic feel for each other, we spoke for roughly 30 minutes, and Sterling asked me if I would like to go out sometime; I said I would like to, and we made plans to go out the following Tuesday. Not 10 minutes later, I had a friend call to confirm lunch plans on Monday. I said, "Sure. Which Monday did you have in mind?" she replied, "This Monday, February 13th". That's when it dawned on me that I just made a first date for Valentine's Day. Fuck. Sterling called on Monday to confirm plans with me. I mentioned I didn't know Tuesday was Valentine's Day when we made plans and asked if we could do it another night. He agreed, and we made plans for the following day instead.

When the day rolled around, I was awoken at 6:00 am by a friend and publisher who needed significant help, like 5-alarm emergency major help getting a project submitted by midnight. Still, there is no way I am postponing this guy again. I don't want things to get ridiculous. So I put my phone on silent and pumped out 20 hours of work in 11 hours. I finished up around 5:00 pm and checked my phone to confirm plans with him. I see I have a few missed texts from him, the first telling me he's looking forward to meeting me (awe) and then another making sure we are still on, and finally one saying never mind. NEVERMIND. I text back, "nevermind????" and he sends a text saying he thought I was blowing him off, but he's still on for dinner if I am. Instead of agreeing, I got offended that he dismissed me so quickly and told him I thought we were not a match; good luck. Did I mention I started my period that day?

This is a story of a first date, so I am still thinking about this guy a few days later and genuinely regret not meeting him. Now in everyday social situations, people describe me as charismatic and outgoing. When I like a guy, though, all those social skills go right out the window, and I behave like I have never spoken to another human before. I boldly decided to call him up and apologize and see if he would still like to meet. So I dialed him up, expecting he would not even take my phone call. He answers on the first ring, enter nervous panic feelings. I say who I am. I apologize and ask him if he would still want to go out sometime, and without hesitation, he says yes. I was in shock to the point I asked him, "Are you sure?" yes, I really said that. To reiterate, no social skills in circumstances involving a guy I like.

The day of the date arrives, I have a light workload, I am feeling good about it, I am mentally and emotionally prepared, I have my clothes picked out, and everything is good. I get dressed, do my hair and my makeup. I looked great. My makeup might have been the best makeup I have ever had, not done by a professional. I was glowing. It looked like someone had airbrushed me on a magazine page. It had been raining on and off most of the day, so I left a little early. There is an accident that delays me getting on the freeway, but it's not so bad. I am looking at being about 8 minutes late.

I text Sterling, letting him know. He says no worries, he's there and will wait for me outside. This is at roughly 7:15 at this point. The rest of the drive goes smoothly, and I get there right at 7:38; awesome. I drive around for a bit. Parking is tighter than I had anticipated. It's a part of town I rarely go to. Now it's 7:45. He texts that he will go ahead and get a table. I text back, saying that sounds good and that I am just looking for parking. I eventually found a parking garage at a reasonable distance. I park my car, and in front of the parking space on the wall is this little placard that states, "Please prepay and display ticket on dash or vehicles will be towed." I get out of my car and head towards the ticket kiosk, where there are roughly six people in line waiting to pay, six people. I can only imagine what I must have done in a previous life for this kind of karma to play out. On top of the massive line, the card reader on the machine is down, and you have to use cash. Luckily for once, I had cash. The people in front of me are trying to stick their damp flaccid one-dollar bills in, constantly rubbing them on the corner of the machine and praying to their various Gods for the machine to accept them. I finally get a ticket, place it in my car, and walk towards the restaurant.

As soon as I leave the shelter of the car garage, the sky falls out with a nice gush of rain because, after everything else, I really need to show up with wet hair and damp clothes. I am using a phone app to find my way. Now I am shivering from the cold rain, my sandals are sliding around on my feet, and I'm on the verge of tears when he texts me, "I am ordering a margarita," now, honestly, if this had been any other date. I would have just given up and ghosted him so hard he would begin to question his own existence. I like this guy, though, and a lot has gone into getting us to this point. It has been 20 days since our first convo. I find the tiniest of overhangs and text him my location and that I am soaked and walking and proceed to the meeting place. It's close to 8:00 pm, which means I am thirty minutes late at this point. I hate being late. Being late is one of the rudest things you can do to a person. It says, "My time is more important than yours," so now not only do I look like a soggy wet mess, I feel like an awful human too.

I finally make it to the restaurant and see him, and he is perfect. He looks like a Christmas morning. His hair is perfect, his glasses are adorable, and when he gets up to greet me, he smells heavenly, basically the opposite of me in my current form. Now at this point, an average person would have gone to check their appearance in the bathroom, but not me. I had kept this man waiting for 30 minutes. I was going to sit down, turn my phone off and give him my attention because that's what he deserved. As soon as I sit down, the waitress shows up and asks if I want a margarita, they are two for one, and I say, "Sure, bring them both" She starts trying to explain they are on the rocks, blah blah blah, I don't care I would chug prison hooch directly from a colostomy bag at this moment.

She comes back. I kid you not, in less than 2 minutes with these drinks, now remember he had ordered a margarita before I even got there, and it still has yet to arrive. Come on, restaurant, please I am already on a first date which is awkward enough on its own. Can you help out with a bit of service? Is this so much to ask? Hint, it was. He had to track down the waitress to get his drink, then, as if that wasn't enough, she never returned to the table. We had to pinch a server from another table to order food.

Aside from all the disasters, we are having some pretty decent conversation. Sterling is articulate and engaging. He laughs at my jokes. What more can a girl ask for, right? We finish the meal, and I almost feel like I may have pulled this date out of the ditch. I go to the bathroom, and I check out my appearance. Everything considered, it wasn't bad. I attempt to put my phone in my cardigan pocket and return to the table when I realize I had been sitting there the whole time with my sweater on inside out. I turn my sweater the right way and exit back to the table. He tells me to have the waitress run his card for the check, and I agree mindlessly. I meant to pay, but because I was so flustered about my sweater, I just had a derp moment. Then the card is run, and I mention I wanted to pay (can I be more awkward?). He tells me I can leave a tip, so then I pull out all the cash I have left after paying for parking, which is damp, like the middle of summer boob money damp.

As we walk outside, he asks where I parked, which is, of course, in the opposite direction of him because where else could he have possibly parked considering the direction of the date thus far. He asks if I would like him to walk me to my car, I tell him he's welcome to come, but if not, I can find my way with no worries; that was a lie, though, because I have the worst sense of direction of anyone you have ever met. Still, I wanted to seem capable for a whole 5 seconds in front of this man. I was giving him an out to ditch me quickly here because who could even blame him? Luckily he decided to come with me. I make a joke acknowledging my sweater being on backward. He totally diffuses it and makes me laugh. I almost feel comfortable for a second. We get to my car, and I offer to give him a ride to his car. He accepts. I pull over to drop him off in front of his vehicle, curbside. He tells me he had an excellent time, and I tell him the same.

He then leans over for what can only be the friendship hug of death. I was expecting it. I certainly would be giving myself the friendship of death after that disaster masquerading itself as a date, heck I would have probably left the restaurant while I was in the bathroom. Usually, the end-of-date friendship hug of death doesn't bother me. Still, I would pause for 2 seconds before choosing Ryan Gossling over this guy, so I might have been visibly bummed. I find myself leaning in for this hug, and I notice his face is getting closer to mine. Now in my mind, this can only be one of those side-cheek kisses and hugs, so I give him my cheek. Only to realize he was tracking my mouth, INTERNAL FACEPALM, now instead of simply kissing him, believe me, I want to kiss this guy, like stick my tongue in his mouth until one of us practically passes out kiss him. Never one to pass up an opportunity to do the most awkward thing possible, I said, "Oh, we are doing this," and then gave him a peck on the mouth. A peck so dry and horrible, your grandmother would be offended to receive it. Afterward, he practically jumped out of the car, like he was trying to land on the spider wall on American Ninja Warrior.

Now you are probably wondering if he called, he did not, which admittedly makes me sad, but it's understandable. Though a little confusing, why initiate a kiss with someone if you aren't attracted to them? Kisses on the first date are rare and usually indicate a good time by each party member. After a few days, I gave up and redid my dating account because why not? There is no way I can go out on another date that disastrous (crosses fingers). I called and talked to my male bestie about the date. I had genuinely enjoyed Sterling's company and was disheartened to not hear from him. At the very least, I could have been friends with this guy. I tell the story, and he talks me into texting him, assuring me that no man would put his lips on a woman's out of politeness. He probably thinks I was trying to reject him with my whole cheek turning. So I texted him, asking if he would be up for round two. Since I received no reply, it's safe to say he's not down.

Don't feel too sorry for me. I had drinks with a cute doctor 4 nights later, that texted me the next day at 9:00 am. He's intelligent, funny, a Jeffrey Dean Morgan doppelganger level of attractive (can I get an amen?), and best of all, he has horrible taste in women. I feel like Sterling did me a favor here, not because my next date was so awesome, but because he wasn't the person I envisioned him to be when I pre-imagined our summer vacation to South Korea. I often find myself projecting who I think the person is onto them rather than seeing them for who they actually are. That person would have texted back if only to say, "Hey, sorry, I didn't feel a connection." The rejection, it hurts, but I am glad I did it. Life is too short not to take risks.