A Night in Jail
Sequel to Eight Lessons, One Night
I’ve never been someone who has felt brave enough to go up to men in bars or even coffee shops. If they initiate a conversation with me, then I’m fine, but if not, then I’m super shy. If I see a cute guy and we make eye contact, I swiftly look away! I can be the worst at making it known I’m interested. So, it is helpful to have a friend who enthusiastically wants you to find love. This kind of friend I have and is the one who initiated this story with The Suit.
This fella is a sequel to Eight Lessons, One Night. If you read it and remember, on the night in question, my friend decided to spontaneously host a speed-dating event for me in the club. Out of all the men she pointed out to me, there was one guy that was with his bros in the booth beside ours. I actually clocked him before my friend asked me about him.
Just before our group decided to hit the dance floor, my friend asked what I thought of The Suit. I said, “Oh he’s so [insert adjective]!” I can’t remember what I said but it was likely “cute” or “handsome.” As we were all scooting along the benches to get out of the booth, my friend leans over to the other booth to ask The Suit the three questions she asked every guy before matching him with me on this night of speed-dating,
“How old are you?”
“Do you have a job?”
“Are you single?”
He was a year older than me, worked in finance, and was single! She immediately said, “Have you seen my friend?” I casually turned around and smiled at him—being tipsy helps me be brave (or not overthink). I like to believe that smile locked things in because he came straight over and said, “Can I buy you a drink?”
We found a corner to chat, which is very hard to do in a club with music banging off the walls. But that just increases the intimacy as you have to lean in closer to hear each other. I remember laughing at something he said and reached out to touch his arm.
Contrary to what some may think, we talked about more than the superficial. I learnt about his family, where he grew up, and how much he loved being an uncle. Then, it was time for the next guy my friend had lined up, so we exchanged numbers and I continued on with the weirdest night I’ve experienced to date. If you haven’t, definitely read Eight Lessons, One Night because it will fill in some of the blanks.
The following week, The Suit and I went on a date. He took me to a bar that I refer to as dingy. I love a good hole in the wall bar, but this was kind of creepy. I try not to judge too much on a first date, mainly because there’s always going to be an awkward moment and everyone is nervous! So, I ignored the drunk guy sleeping at the bar, the sticky table, and trampled on carpet.
What I haven’t said yet is I went on this date only two days after things ended with The Waiter (from Eight Lessons, One Date). People kept saying, “Who cares about [The Waiter]! Best way to get over someone is to go on a date with someone else.” I know that’s not how the saying goes, but I have never participated in hook-up culture and my friends knew that. Hence the slight adjustment to the saying!
So, back to the dingy bar date. We found a table amongst the two dozen that were free (not a very popular place) and grabbed some drinks. I honestly have zero recollection of how the conversation went, because the whole time I was thinking, “I’m not ready for this.”
A year later, I walked into my local coffee shop and stood in the queue to order. In front of me was a man and woman who seemed to be on a first or second date. The man turned around and I remember thinking he looks familiar, but I didn’t think too much beyond that. As I got to the counter, my friend was working and we began chatting. In the corner of my eye, I see the man leave his date and walk by me to get back in the queue. I can see he keeps moving forward and then looks over at me. I was kind of getting creeped out until he said, “I think we’ve met before.” I played dumb, mainly because I couldn’t place him. That was until it dawned on me.
This man was The Suit!
“Ohhhhh yeah, we went on a date last year,” is what came out of my mouth. That then started us catching up and me being surprised with how much he remembered about what we had discussed over a year ago. I looked over his shoulder at his date curiously looking at us and began to feel bad, so I said, “Well, I’ll let you get back to…” and waved in the direction of the date.
The minute he walked away, the cafe crew was all ready for the tea! I filled them in on the backstory and to my surprise, they all approved of me trying a second first date. And if I was honest with myself, I wanted to try too! He just felt familiar and easy to connect with. So, when I got home, I found his number in my contacts and texted him. He asked me out on a date right away!
*big sigh*
I won’t go into details, but he did share why he spent the night in jail. I felt bad for him, but as my sister said, “That is not your problem!” Leave it to my sister to give it to me straight, but that’s because she knows me. She knows I’m too nice and I would go above and beyond to help someone. But, this was not my problem to solve. The Suit and I said our goodbyes and I never heard from him again.
Editor’s Note: This is not the first dude I’ve run into that I’ve gone on a date with. Would you believe that I have run into five? FIVE! You'd think I lived in a small town with those numbers!