As I’ve mentioned before, when working the night shift, one doesn’t always make the best decisions. Still nursing a broken heart (ha! see what I did there?), I’ve done my best at trying to keep as busy as possible over the last several months. And with V-day fast approaching I was not going to spend it sitting at home on my couch watching Bridget Jones’ Diary. So, after perusing the Eventbrite app and seeing all of what my city had to offer on Singles Awareness Day, I closed my eyes and at precisely 1:39am I hit the ‘purchase’ button for a ticket to Be My Valentine – Boston Speed Dating.

Yup, that’s right.

Now, any knowledge I have re: Speed Dating is limited to what I’ve seen on episodes of Sex And The City and in the movie The 40-Year-Old Virgin (I still laugh to myself when I meet someone named Gina. Anyone else?). So I really had no idea what I was getting myself into. As 8pm approached, I never thought of canceling. I didn’t feel nervous. Maybe I was still delirious from the lack of sleep but I put on my big girl shoes (specifically, booties by Fergie) and headed out.

When I walked in, I registered with the ladies running the event and got the low down on how it was going to work: the ladies would stay seated the entire time and the guys would be the ones to rotate. We were to write each other’s names and numbers on the scorecard and then rate how it went. We would be notified the following day of any matches.

The Scorecard

From there, I headed straight over to the bar. A quick look around the room at the gentlemen who were already there and I decided there was no way I was gonna get through this sober. Glass in hand, I took a seat near a friendly looking woman and started chatting her up. Yes, she had done this before. Yes, it is sometimes awkward. Yes, the drinks will help (she recommended a minimum of two). “The best part”, she told me, “is that if the guy is a weirdo, you only have to talk to him for a few minutes”. Perfect. I could handle this. I gulped down my Whitehaven, put on my best smile and we were off.

My first “date” was a relatively normal, attractive guy. And before sitting down he asked me if I wanted another drink. Perfect. Maybe one could find love here. However, when we got to the bar I got a little nervous. Does he pay for my drink? This isn’t a real date. Should he have to invest $12 in a glass of wine for 5 minutes of smalltalk? I didn’t think so and I made sure the bartender charged my drink to the tab I had opened. Back at our seats, we got to talking – he explained how much respect he had for nurses as his mother/aunt/sisters were all nurses. I was interested as to why he had a red rose made of chocolate in his suit pocket. But before I had the chance to ask him, it was time to switch.

The next guy sat down and one look at his short-sleeved button down shirt covered in American flags and images of Mount Rushmore, I had a feeling he wasn’t my kind of guy. Then, after he sat down and his opening line was, “So, how many bathrooms do you have in your house?”, I knew he wasn’t my kind of guy! <Sidenote: He had six. I only have one. I mean, how many should I have? Do one need a backup? I digress.> Trying to pretend like I hadn’t heard the question, I remembered what my “friend” had said at the start: if they are weird, it’s only for five minutes. So I had polite conversation with him and I even took away a fun fact: George H.W. Bush was born in Milton, MA. Well, who knew! I made a note to myself to pull out that little nugget in case of future dating emergencies (i.e. awkward silence, inappropriate questions). Pleasure to meet you, sir…but you’re not quite my type. On to the next.

And the next. And the next. There continued to be some some awkward moments. Like the guy who sat down and commented on the choker the girl he was just talking to was wearing. She overheard this, looked at me and said, “This guy is a jerk and you shouldn’t talk to him”. Thanks for the heads up, girl. Or the guy who sat down and said he hoped I was “more normal” than the last few girls he had sat down with. “Normal?”, I asked. “Yea, like you don’t have any kids do you?”. No sir, none that I know of. And I left it at that, deciding not to get into the fact that having children is generally considered to be a pretty normal human activity.

At the risk of sounding old, with about 40 people trying to speak to one another, it was quite loud which made it difficult to hear my potential suitor sitting across from me and get the proper pronunciation/spelling of his name for my scorecard without shouting. By the time it was over, I had had enough. I realized I had said the same thing on repeat for the last hour and a half: “Hi, I’m Jacqueline. Nice to meet you. What do you do for a living? I’m an ICU nurse. Yes, its intense. But yes, I do love it. Where are you from?  I grew up about an hour south of the city. However, I’ve lived in Boston for about 15 years.” So I somewhat understood when date #17 sat down and even before introducing himself stated, “I just want to go home.” Nice to meet you too, buddy.

Tired of saying the same thing over and over again, I started to begin the conversations with, “What brings you here?” And I got several different answers. Some were serious about finding love. Others had recently relocated to the area and were looking for a partner to explore the city with. And still others were there because their roommate had forced them to come, one guy had been invited back after an unsuccessful matching at the last event and another man seemed to be using the event (or at least the majority of his time with me) as a therapy session.

It certainly wasn’t all bad but it’s safe to say that I was never inclined to check the box ‘Definitely Fancy A Go’. I had some short and sweet conversations with many of the men. Most of the guys were polite and easy to talk to. Some were mature, intelligent and good looking but not quite my type. Others were immature and therefore, also not my type – surely I’m referring to the group of guys I had witnessed performing wrestling moves on one another at the bar when I had first walked in.

So, despite the fact that I did not have my full wits about me on Monday night at work when I purchased the ticket, I was glad I went. It got me out of the house, out of my comfort zone and gave me the opportunity to reexamine and reignite my dating skills. Now, will I do it again? Probably not. But I will definitely recommend it to my girlfriends looking to give themselves a little kick in the ass.

The night ended on a high note when I had the opportunity to ride home with my Uber driver Nancy – a very sweet, happily married (for 26 years!), mom of three. After finding out where I had been for the last two hours, she was inquisitive and excited to hear all about it. She patiently listened to me vent and when we arrived at my apartment she turned around, looked at me and said, “Don’t worry, kiddo. You’ll find someone.” It was so genuine, heartfelt and motherly that I think I believed her. I immediately got on the Uber app and sent the ‘good conversation’ compliment as well as five stars her way.

Update: I just received an email saying I matched with three guys. The email included their names and email addresses. I’ve already received an email from one of my matches who remembered specific details about our conversation. Impressive. I, on the other hand, can’t remember a thing about him. I mean, I remember most of the conversations I had, but to put a name with a face after 20 mini-dates that were each very much like the one before it? No. I cannot recall who he is, what he looked like or what we talked about. I can only hope that the Savy B didn’t cloud my vision and I did indeed check off the correct box. I’ve responded and agreed to have a drink next week. I’m positive hopeful I’ll be able to pick him out of a crowd in a bar. Stay tuned…