“One of the reasons some people still risk the possible horror of a first date is the possible magic of the goodnight kiss at the front door.” ~ Carrie Bradshaw

72 hours. Three first dates.

Yep, I’m exhausted but I did it. I was actually scheduled to have four dates this week but had to reschedule someone as I simply cannot do another 2 hour conversation of “where are you from? what do you do? do you have siblings? how do you find dating in nyc? what does your typical weekend look like?” Going on three in three days has definitely taught me some things about myself and others. 

Date #1

Stats: Financial Planner, early 30s, 6’0

I knew he had a sense of humor before we went out as he’d already made me laugh a couple times with quick one liners over text conversation, so I decided that even if the date didn’t result in sparks I could at least have a good time over a couple drinks. He chose a spot in my neighborhood (the only place that I actually hate because the food is disgusting), I arrived at 7:01 for our 7 o’clock date. He texted to let me know he was running “7 minutes behind”, so I grabbed a seat at the bar….and then I switched to another table. On a first date, seating arrangement, proximity to other people, etc is very important in trying to make things as ‘not awkward’ as possible.

He strolled up at about 7:10 and thankfully he looked just like his pictures (I always have this fear that “this time” is the time I’m going to get catfished). Cute, not Ken doll cute, but cute enough. We hugged, ordered drinks and proceeded with what I like to call the interview. Firing off questions with a few laughs in between, the conversation flowed easily. He was funny, intelligent, and could hold an interesting conversation. We sat for two hours and hugged goodbye with a quick kiss on the cheek as I hopped in a cab.The next morning he texted me that he had a really good time and would like to do it again if I’m interested. In comparison to most of the first dates I’ve been on this was a home run (no eating of my face, no attempted suicide stories, no professions of love) so I am definitely up to see him again.

Date #2

Stats: Civil Engineer for private equity firm, 30s, 6’0″

I was a little concerned about his looks, not because his pictures were beastly. There was just something about his mouth area that was…off. I know that sounds weird but his mouth looked weird. I couldn’t put my finger on it. He had both smiling and not smiling pictures but there was something about it that just wasn’t doing it for me. He seemed like a nice enough guy so we met at a spanish wine bar not too far from my place and pretty out the way for him and I appreciated the effort in making things easy for me. He’d just got back into town from a work trip a couple hours prior and when I walked in at 7:01 for our 7 o clock date he was already seated at the bar with a glass of wine. Punctual, I like it. He gave me this sheepishly awkward hug and pulled out a chair for me and off we went, firing away our interview questions.

Within the first few words I figured it out. His bottom row of teeth were fighting each other. Not like ‘girl fight’ slapping, hair pulling….more like MMA kicking your ass till you’re bruised and bloody, fighting each other. I don’t think I’ve ever seen teeth go in the directions his do. I could not stop staring but did my best to try and look in his eyes and not at the mess going on in his mouth. He was probably the corniest guy I’ve ever been out with, and that’s saying a lot. Not in a nerdy way just in a cornball, ‘I awkward laugh and make weird faces at my own jokes’ kinda way.

He also almost started to cry when he told me his parents died two weeks apart from each other when he graduated from college. Umm, wow 😦 #awkwardmoment.

After a few glasses of wine, we started to leave and he mentioned that he would love to do this again sometime soon. At that moment I thought, sure I could do this again, but I was really saying it as though I could do this for HIM again. In reality, there was zero spark on my end and I’d be perfectly happy never seeing him again. I haven’t spoken to him since.

Date #3

Stats: Logistics; early 30’s; 6’1″

At this point, I was exhausted from the two nights before but it was too late to back out. I tried to convince one of my friends to go as me, she rejected my requests (some friend). So, off I went. He’s new to NYC so I had to pick the place, an italian wine bar halfway between both of our places. We agreed to meet at 8, at 7:55 he texted me – “sorry, got off on the wrong stop. be there soon.” I walked in at 8, found a spot for us at the bar and waited. And waited. Annnnnnnd waited. At 8:19 I got a bit concerned only because he’s new to the city, otherwise I would’ve left at 8:20. Instead, I texted him to make sure he was ok. He responded: “Yea, sorry I’m an idiot. I’ll be there soon”….buuuuut you said that 25mins ago -__-. I decided that if I finished my more than half empty glass of wine before he arrived I was going to leave. At 8:29 he walked in, just in time. He apologized, clearly embarrassed about getting lost and ordered a glass of wine.

The conversation flowed easily, he’s not my usual type personality or looks wise but he was a nice guy. Easy to talk to, respectful, seems like he has a pretty easy going persona overall. About an hour into the date he asked if I’d be open to grabbing a bite to eat. I was a little caught of guard but I wasn’t having a bad time and seeing as though I was planning to grab some food to go once I left him, I figured why not. We walked a few blocks to a sushi restaurant, chatted some more and shared a few sushi rolls. He gave me a quick hug and said he’d like to do this again sometime and to let him know if I’m around….I’m not sure how I feel about him but I may give him another chance to see if theres some spark.

There’s another guy that wants to go out tonight but he gives me a creeper vibe, he’s called me baby three times. I.e. “So when might I be able to buy you a drink baby?” “Good night, sleep well baby. talk soon ;-)”

I think I actually gagged out loud when I read that last one. When I rescheduled our Monday date he responded – “I know you will be well worth the wait ;-)” *cringe*

He also kinda has the face of someone you’d see on Nancy Grace as a suspect in their missing wives case. I’ll let ya know how it goes.


10 thoughts on ““One of the reasons some people still risk the possible horror of a first date is the possible magic of the goodnight kiss at the front door.” ~ Carrie Bradshaw

  1. “I tried to convince one of my friends to go as me, she rejected my requests (some friend).”

    literally made me laugh out and spew up my coffee. great blog!


  2. hahah Date #2 was the best shit I’ve heard in months. I applaud U for your consecutive speed dating.. staying tuned to next weeks dating spree . Please don’t go missing in the mean time . k thanks lol

  3. Three dates in 72 hours? Wow! You’re a glutton for punishment. (Says the girl who hates dating.) Thanks for allowing me to live vicariously through you!

    Maybe you can talk someone into meeting #4 for you… a professional female boxer sounds about right because he does sound like a creeper. 🙂

    1. lol I know right?! I have no clue why I thought that would be a great idea, and yea, I definitely would need a bodyguard for mr. winky face. Thanks for reading!

  4. Love your stories! I have done the three dates in 24 hours and it is rough. It is so hard to keep up with all their background information and stories. Way to hang in there!

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