The Next First Date
- May 7, 2015
- 7 min read
Being back on the dating market meant actually going on a first date. And woo wee, I was out of practice.

I did it. I hit submit. I officially made an online dating profile. Satisfied with my craftily created answers I put my phone on the charger and smiled as I lay my head softly upon my pillow, welcoming the dreams of broad shouldered men from different cities with McSteamy bodies and McDreamy hair (may they rest in peace- yes, I still watch Grey’s). I dreamed that in the morning, I would awaken to messages from soulful blue eyes, Mad Men inspired jaw lines, well traveled, well versed, well intended gentlemen with interesting stories and kind smiles. I was enjoying my nighttime merriment of men. Ah, this is the single life.
The sun rose in the east (ya know, as it does every morning) and it peeped through my window, slowly filling my room with the warm glow of manly possibilities. I reached for my phone, anxious to discover who would be drawn like a moth to the flame of my optimistic smile and effervescent energy. Yes, online dating would open my life to the wonders of exploring the vast market of eligible and worthy men.
I have one message. No worries, interesting men are often busy filling their lives with adventures. It might take those moths a while to get to the flame. Still, I had one message. Someone was already interested a mere 8 hours later. I opened the message.
“I want to put my dick in you.”
…
You’ve got to be fucking kidding me.
As it turns out, my flame was attracting stink bugs. In the next week, I received all kinds of messages from a variety of characters- foreign men looking for wives, couples looking for threesomes, Doms, Subs, a guy in a wheelchair, a full length emoji story, husbands in open relationships… listen, I wasn’t a bartender for long, but I worked long enough to know better than to ever mess with a married man, especially if he says she says she’s cool with it. Hell hath no fury like a woman scorned. Those bitches come ’round with shotguns looking for blood and redemption. I saw that unfold terribly, way too many times. Guys, put the ring on your finger and your dick in your pants.
The eligible market was indeed vast. And exhausting. But did I lose hope? Hell no. Did I delete my profile? Absolutely not. Did I find comfort in chocolate because it would never let me down? Yes.
I also started training for a half marathon. I figured that eventually all that swiping left and right would pay off and I’d actually get to go on a date. And if I was going to start dating again, I better start running again. You know how it is when you’re in a relationship, you can get a little lazy, a little soft if you will. But I’d run a half marathon before and my ass never looked better. This former soccer player with Italian thighs was able to rock a pair of skinny jeans or a mini skirt during training and I’ll be damned if I wasn’t going to pull those out of the depths of my dating wardrobe. My half-marathon-get-in-dating-shape-plan was working, and just in time to get back on the market.
Sure enough, the moths did begin slowly fluttering in. I swiped right on a very handsome and very witty pharmaceuticals consultant who played acoustic guitar gigs. It’s a Match! Nice! Did I wait for him to message me? Of course not.
His headline read, “Tall, funny, handsome, humble.” So, witty me wrote, “Tall, funny, handsome, humble… and modest?”
He responded, “Yes ma’am. Nobody gets that joke!”
He was quick and smart and wasn’t afraid to go head to head with me in witty banter. Soon, he asked me for my phone number. All of the sudden, online dating became very real. What if he was not at all who he said he was? What if he was short, creepy, old… and creepy. He would have my first name, my phone number, he could easily find where I worked. What if he was some 58 year old man living in his mother’s basement ready to kidnap me and chop off my toes one at a time and send them to my parents for ransom money?? These things happen in Lifetime movies, they could happen in real life!
So, I did what any sane, single woman who wanted to protect herself would do. I Google stalked him. His username was TomWit. So, I typed in “Tom Wit Guitar” and just like that, there he was, Tom Witkowski on LinkedIn and on YouTube, consulting pharmaceuticals and strumming ditties. This is why you’re not supposed to use any part of your real name as your username. Good thing I’m not a creeper. I just Google stalk my internet dates in my free time. No big deal.
Then, it happens. “Want to grab a drink sometime?”
I just got asked out on my next first date.

It was Wednesday and unfortunately, we did not have a mutually free weekend for the next month. He suggests, “What about today? Come meet me after work for a drink.” I hesitate. I look down… through my glasses. You couldn’t have at least put your contacts in today? A pair of skinny jeans, a green army jacket, camel colored flats. Oh yeah, and an ankle brace and a set of crutches. Remember that fool proof half-marathon plan? It was all well and good, until I sprained my ankle. That’s right. Three days before the race and my ankle was swollen. I ran the race anyway, of course (I wasn’t going to do all that training for nothing) but I ended up unable to walk without crutches for a month. And because of that, I couldn’t carry a bag at work. Nope. I had a backpack. I hadn’t bothered putting on much makeup that morning, in fact, I don’t think I even washed my hair. So there I was, glasses, crutches, ponytail, and backpack, ready to reintroduce myself to the dating world. Yup. I was back on the market.
“Sure, ” I replied. “I just need to stop at CVS to get some more Tylenol for my ankle.” By Tylenol I meant eye liner, blush, mascara, breath mints, and a hair brush. I popped in the mints, teased some of my hair, quickly applied the makeup in my rearview mirror, praying the lighting in my car was being honest, and rushed out of the parking lot.
This could have gone one of two ways: I could enter the bar, the wind slightly blowing through the door, gently whisking my perfectly voluminous hair out of subtly glowing face, my eyes highlighted reflecting flecks of green and blue, distracting him from my off-balance swagger. Or I could stagger through the door with cheeks far too flushed and hair in a beehive, lookin’ like a hot mess drag queen Tiny Tim coming down for Christmas dinner. Hoping for the best, I leave the crutches in the car and hobble into the bar.

And there he was. Tall, handsome, he smiled at me. And at that moment, I realized I had forgotten how to date. Do I kiss him hello on the cheek? Do we shake hands? Do I do nothing? I hop up onto the barstool and the bartender comes over. Do I look like a priss if I order water first? Active girls need to hydrate! I order water. And a beer. He’s nice and he wasn’t lying, he is funny. But am I laughing too much? I’m definitely laughing too much. He asks me about where I live. Do I mention I live with my parents? Do I dare bring up the cats? I try to act casual and catch myself touching my hair. Do I seem ditzy? I can feel my cheeks getting red… or redder. I still wasn’t sure if my rearview mirror application was appropriate. It’s definitely time to wash my hands - that’s what I say when I need a second to get my shit together, or text a friend.
“Help! I don’t know what I’m doing!” “Yes you do. You’re fine. You’re just not used to this. Is he cute?” “Yes. Very.” “Good! When he stands up grab his junk.” “YOU ARE NOT HELPING!” “I’m kidding! Go have fun and call me when you leave!
I take a quick glance in the mirror expecting RuPauls’ distant cousin to look back at me. But no, there I was. Just me. Happy green eyes and pink cheeks. I smiled my big, joyous smile (mostly to check for food in my teeth), but it was me. Back on my feet, well, one foot, and back into dating. Girl, you got this. I flipped my hair upside down and brushed my fingers at the crown to give it some umph. While I was down there, I checked under the stalls for feet. Empty. I flipped my hair back up, looked at myself in the mirror, and with a spirited arm wave and a loud snap, said to the me in the mirror…

Another hour and another beer later, I got back to my car and was sure I blew that date. I felt a little awkward and it must have showed. But that wasn’t the point. The point was, I did it. I went on a date. I didn’t get kidnapped, I didn’t lose any toes, and now that I’d gotten that out of my system, I’d be ready for what the dating world would bring me next.
The next morning I sleepily opened my eyes as the sun (once again) peeped through my window, bathing my room with the warm glow of dawn. I reached for my phone to check if I had time to snooze. I had one message. It was Tom.
“So on a scale of 1-10 how much did I talk about myself yesterday? I get awkward around cool girls. Next time, I’ll be my normal awesome self. I swear :)”
And Tiny Tim is back in the game!
Want to hear his side of the story? Check out Welcome Back: The First Date’s Response
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