TBT: The First Date

App: Bumble

Name: Miles*

Date Location: Strange Brew Tavern – Manchester, NH

Location Review: 3.0 Stars – If you’re a beer person, absolutely recommend. There’s tons to choose from. It’s great for week nights but I wouldn’t recommend for weekends. You end up in a room which looks like a frat house basement and run into people from high school.

Date Duration: 4 hours

What Happened:

After my 6-year relationship ended I had no idea what to do. I never “dated” since my ex and I got together in high school then stayed together through college. All I knew was that while I lived with my parents and only hung out with female friends, I needed a way to meet men.

I downloaded dating apps and one night was swiping through Bumble. I matched with Miles* and we began chatting. Based on his photos, he was pretty cute, outdoorsy, and liked to stay relatively active. I asked him out and we went from there.

Little thing to note, we had talked A LOT on the app. Since this was my first attempt at dating I wasn’t sure when to bring up a date or if he would do it himself. So we had already covered a significant amount of ground before meeting up.

After nearly peeing myself from nerves, I made it into the bar. He did not look like his photos. I could bench press him. But hey, he seemed like a nice guy and I have no idea what dating is so FUCK IT.

He was really sweet. He found out that I co-hosted a morning radio show and he told me that he listened in that morning. Also when he found out that I love Straight Outta Compton he listened to the soundtrack on a trip up north with his friends.

But after a few drinks, I kinda knew this wouldn’t go anywhere. He had that “lives with his mom” quality and since we already covered so much ground, had nothing else to talk about. Because I didn’t want my first date to be a bust, I went full Resident Assistant and pulled questions out of thin air.

Despite him making a “Wow, we had such a great date since it was 4 hours” comment, I never heard from him again and I was so happy about it. I had done the impossible. I went on a first date and didn’t get murdered. I did something I never thought I would have to or even could do. But I did. And it opened a new door of my life. THANKS MILES.


Encounter #4.1: The Struggle

App: Tinder

Name: Shane*

Date Location: Low Fidelity – Jersey City

Location Review: 4.0 Stars – Hand-crafted cocktail bar with options that won’t intimidate and has corn hole in the back.  Quite the gem in a shithole.

Date Duration: 4 hours

What Happened:

Once again, I started this date on the fence. I couldn’t tell how attractive he was by his pics but we had decent banter going so the possibility was there.

Shane was a shapeshifter. There were some angles where he looked really good and some not so much. He was over 6 ft which helped his case and fun fact: is blind in one eye. What really got me was that he lived in Jersey City and was only a 10 minute walk from my apartment. Pretty much everyone I have met in NYC shits on NJ and thinks Jersey City is insanely far when it’s 40 minutes away (it can take 1 hour to go from the Upper West Side to the Upper East Side. JUST SAYING).

The thing with Shane is that he was boring AF. One sentence answers, not particularly funny, and didn’t ask too many questions. I can’t carry the whole team on my back, bro. Despite that, he was fine. Did bring up that he makes 6-figures which rubbed me the wrong way, but was fine.

I think my standards for a good first date are very different from other peoples’. Just because we may spend a decent amount of time together doesn’t mean it’s good. I may want to dip after 5 minutes but the opportune moment doesn’t come up until 3 hours later. Your girl plays the long game.

But this was the case with Shane. We were finishing our last round and he says, “Wow, we’ve been out for 4 hours. I’d say this went pretty well. I had such a good time..Let’s do this soon blah blah”. If by well you mean I got drunk from chugging my drinks during the awkward silences, then yes. It went swimmingly.

Once again though, I did shit I shouldn’t have. We were walking in the same direction to go home and I may have made out with him on the corner. Typically I’m not a first date kiss person never mind with someone I’m not into, but god damn it’s been awhile and Mama needed something to hold her over.

Too many times I’ve heard the story of, “When I met my husband for the first time I couldn’t stand him. But for whatever reason I gave him another chance and now we’re married”.  Keeping that in mind, we texted for the next few days and since he could keep decent banter I agreed to a second date.


Situation #3.1: The Wedding Date

Name: David*

Location: Friend’s wedding in Maryland

What Happened:

When being invited to a wedding there are 2 strategies:

  1. Find a boy to go with you
  2. Take one of your girls so you can get some action

Went for Option 2 and brought my girl Katey. Before even heading to the wedding, Katey asked what my intentions for the wedding were. I said to make out with hot boys and dance my ass off. That mission was accomplished.

We get to the ceremony and I remember looking across the way and seeing a group of cute guys. Target acquired: just needed an opportunity to strike. During cocktail hour the stage was set. It started getting windy and I was helping someone clear a few tables in the corner. I started combining glasses of champagne and then I hear, “Oh, those aren’t going to waste are they?” I look up and there are the cute boys from earlier. I hand the glasses over, say to double fist, and we clinked glasses.

When the dance floor opened you know Katey and I headed on over. We were breaking that shit downnn. And then the boys came over. Out of the group, there were 2/3 really hot ones. Like 9s. Weddings are cool. They bring out the feels in everyone…as does copious amounts of beer.

One guy in particular, David, made his move. We danced and kept getting closer. It got to the point that the bride came up to me and said, “Those are some of my husband’s closest friends. They’re all great guys. Have fun tonight!” Oh, we did. Within a few songs we were making out, he was grabbing my ass, and kissing my neck.

We walked around holding hands and kept making out. However, something happened. I eat very clean normally. I didn’t that weekend. So while we were outside I let out the most ripe fart of my life. David turned to me and starts saying how it smells really bad outside and we should go in because it smells so bad. …I said nothing.

Despite my party foul we kept dancing, making out, and then the reception was wrapping up. Katey and I were going to head out for donuts and go home but David and his friend asked for a ride to the casino for the after party. It was on the way so we drove their drunk asses back. David found me on Facebook in the car and pointed out the fact that I look hot in my profile pic but it looks nothing like me in person. COOL.

Aside from that, I thought he was really cute and it’s not often I find a man who can keep up on the dance floor. So I messaged him, we talked for a day or so, and that was it. Well, until September.



Encounter #2.2: Hat Guy

App: Tinder

Name: Dan*

Date Location: Pier I & Central Park

Location Review: 4.5 Stars – Beautiful summer spot. On the water and you can order food (and full bottles of wine) at a stand then bring it to your table. Plus lots of people walking their dogs.

Date Duration: 5 hours

What Happened:

I met up with Dan and he was already ready with a bottle of white wine. A man after my own heart. We downed it and ordered fried snacks. It was such a beautiful place and the sun was going down over the water while we chatted.

Once again, conversation was on point. Rarely do I find that someone meets my standards in this realm. Aside from making me nearly pee myself laughing, we got to the shit and had the past relationship conversation. Also, he kept complimenting me in ways I never have experienced. I was telling him a story of how this guy I used to fuck around with chapped his dick from riding a motorcycle and his response was, “That’s really sexy how you said that. ‘Fucking around’. I like it”. And he caught on to how I spoke and pointed out my “Laura Catch Phrases”.

We walked over to Central Park and he took my hand and pulled me over a fence to watch the cast of Shakespeare in the Park rehearse. I couldn’t tell you how the actors were because we kept making our own commentary and crude comments.

We strolled around for awhile trying to find the area of the park where dogs walk at night but ultimately gave up and sat in a gazebo by the lake. Then things got a smidge awkward.

Everything was business as usual until he said, “You know this is really weird for me. It’s the second date. Usually we’d be getting down right now…Oh I made you uncomfortable. I’m sorry. Taking it slow is different for me but it’s really nice. It’s good”. KAYYY. But who am I to judge? Typically I don’t do second dates so maybe I should restructure my methods.

We walked to the train station and rode the subway together until we had to part ways on the platform and did the “who’s going in to kiss” look. Dan says, “You’re really sweaty. I’m really sweaty. Now is not the moment. I’ll text you later”, we hugged, and parted ways.

He did in fact text me later and we were on for Date #3.


Situation #1.1: Creepy Old Dudes

Name: Craig? and Scotty

Location: Fager’s Island – Ocean City, Maryland

Location Review: 4.5 Stars – I have a soft spot for Maryland but I also love trashy dancing, drinks, and being on the beach more than anything.

What Happened:

My college roommate and I hadn’t seen each other in years and just wanted to dance our asses off. Best place to do that? Ocean City, Maryland! It’s so delightfully trashy but the bars are super fun, there’s tasty food, and lots to see.

We went out to Fager’s to eat and get a few drinks before things picked up. While we were out on the water taking photos these 2 old guys (not the “George Clooney sexy” kind. The “hat-wearing, sunglasses strap, creepy” kind) came up and offered to take our photo. Fine. They take the pictures, we chatted, and found out that they were alums of our college. One even made a comment about how much older they were and that they were old enough to be our dads.

They insisted on buying us drinks and we were broke so we agreed. Then the unwanted flirtation began. We both got uncomfortable and tried to sneak away but they wouldn’t leave us alone. We headed back out onto the water because we, as in my roommate and I and nobody else, wanted to snap pics. Alone. But they came anyways.

Eventually they began asking what we were planning on doing that night. We kept giving the vague, “I don’t know yet. We’re still figuring it out”. But they whipped out the phones and asked for our numbers. FUCK. I put in my fake name and in a moment of wisdom, my ex’s number.

Scotty texted the number immediately and my ex responded. Immediately. Scotty turned to me and goes, “Wow, you already forgot my name. You’re fast though. I didn’t even see you take out your phone”.

FUCK. I pulled my roommate, made up something about needing to shit, and ran out of the bar. I called my ex because alcohol told me to, explained the situation, and apologized. He was cool with it but lesson learned: put your friend’s number. Never a boy’s.