How to Date (Everyone)

When I turned 23, I did so in a gay bar in the heart of New York City -- still in my yoga clothes and clutching both my mat and gin with an equal amount of effort. This was a much different scenario than when I turned 22, laying on a pullout couch in Chicago while eating pretzels and watching One Direction videos with my wonderful friend Ellen and, again, very, very different from when I turned 21, took four consecutive shots of Cherry Burnettes vodka, then immediately threw up at 12:01.

Me after no longer having the ability to relate to Taylor Swift's song "22" and realizing that it IS true no one likes you when you're 23 (and keep accidentally hitting all of the men at the gay bar in the face with your yoga mat).

Me after no longer having the ability to relate to Taylor Swift's song "22" and realizing that it IS true no one likes you when you're 23 (and keep accidentally hitting all of the men at the gay bar in the face with your yoga mat).

The situation in which I'd arrived at a gay bar with my yoga mat was extremely unexpected and impromptu, so I'd assumed that night in February was likely the only time I would ever bring my mat into a bar with me again. But, of course, I would not be writing about this if it hadn't happened more than once -- which, it did, after a night out in August at The Heights.

I've written about The Heights many, many times -- back in 2013, when Chelsea introduced me to what we still refer to as "crack margs" for the first time, when I wrote about spilling multiple margaritas on myself in the span of ten minutes and, of course, it's where I went after Zach Groth ruined my date by very clearly overstepping his boundaries. But, this is because despite the health inspection rating of a "B," it's one of my favorite spots to go in NYC and so, when we were planning a goodbye dinner for one of our friends, The Heights is the place we chose.

There were about ten of us out at dinner that night and, because by the end of a few rounds of margaritas there, I am usually in more appropriate shape to go home than go out, I had come straight to the restaurant from yoga. Even though I'd planned on heading back to the UES immediately after dinner, I am a millennial and therefore suffer from FOMO greatly, so, when everyone else expressed their plans to go to another place, I, undeterred, once again trekked into a bar carrying my yoga mat and a backpack full of sweaty clothing.

It would appear I have still not perfected the art of bringing a yoga mat to bars (though, in all honesty, this may have been contributed slightly to the fact I'd drank an inappropriately high amount of margaritas) and, in attempts to unlodge my mat from under the bar after ordering a drink, I ended up whacking an attractive guy on the head with it. As it would turn out, this method of meeting people is a much more effective move than when accidentally executed at gay bars and so, after a quick apology from me, the guy asked what I'm sure everyone else had been wondering since we'd arrived: "Why would you ever bring a yoga mat to a bar?"

I explained to him that I practiced Bikram and had just come from class, then was pleasantly surprised to find out he wasn't only familiar with the practice -- he was an instructor at my studio. Amazed at the coincidence, we exchanged phone numbers and made a date when I promised to come to the class he was teaching at the studio by my apartment the following Thursday night.

The next day, I was laying on Rockaway Beach with the same group of friends I'd gone out with the night before, where we were drinking wine, eating cheese and discussing dating. At this point, I hadn't gone out with anyone since Sam and I had stopped speaking and our talk that day on the beach made me realize I needed to start going out with men again, even though the thought of going on a date instead of being in bed early for yoga gave me an uncomfortable amount of anxiety. Still, I was feeling pretty alright about the situation since I'd gotten the yoga instructor's phone number the night before and so, I decided to give Tinder another try.

I ended up matching with a guy wearing a Hawaiian shirt whose profile promised he'd deliver on "terrible pick up lines and mediocre sexual experiences."  In all honesty, I'd originally swiped right because I was pretty sure I had the exact same shirt from Urban Outfitters (I've been told I'm utilizing Tinder wrong), but it ended up helping he had pretty stellar eyebrows. We started chatting and, while I generally don't give out my number to many men on Tinder because I'm afraid of Internet strangers ever since I got semi-Internet famous in middle school due to my Xanga devoted to Matthew Underwood from Zoey 101 (long story), Hawaiian Shirt Dude had made me laugh with his profile and also had an appreciation for beer that I could relate to on what may have been a spiritual level. So, I sent him my number. He replied on the app that he'd send me something dirty so I'd know it was him.

I immediately regretted my decision.

A few minutes later, I received a text from an unfamiliar number and, preparing myself to see something awful, opened the message -- to find it literally just said "Something Dirty." Highly relieved I'd received a corny joke instead of another (almost) d--- pic, Hawaiian Shirt Dude and I made plans to go on a date to a bar on the Upper East Side on that upcoming Thursday. My only stipulation was it had to be after 10 (because I still wanted to go to the attractive yoga instructor's class), so I let him know I had Bikram Yoga plans until later in the evening. 

Then, because I am 86-years-old, I immediately fell asleep before midnight.

I woke up the next morning to a text from Hawaiian Shirt Dude, telling me he thought it was awesome I participated in what he referred to as "The P90X of Yoga," which is my favorite description of Bikram Yoga to date. Now, I've been told I'm a pretty terrible texter -- honestly, the only people I probably reply to immediately are my family members and that's mostly because my mom sends very dramatic texts with no previous clarification, like "There was a murder up the block" or "OMG, One Direction is splitting up… going in their own directions." (Both of these texts were equally important to me). But, because of this, I didn't tell Hawaiian Shirt Dude I appreciated his accurate depiction of Bikram until I was already at work and in line to get my daily morning tea with Chelsea.

Hawaiian Shirt Dude was a much better texter than I'll ever be and so, he replied immediately, almost before I'd even received my tea from the Starbucks employees who actually recognize Chelsea and I by name. I glanced down at my phone to read his text, which I'd assumed would include another dad joke, but instead was shocked to see the following message:

Oh, I wonder if you know my buddy who’s a yoga instructor... his name is [NAME OF ATTRACTIVE YOGA INSTRUCTOR I’D MET AT THE BAR].

I was so overwhelmed I almost dropped my tea and pretty much gave Chelsea a heart attack in the middle of Starbucks from the sound of my sharp inhale. It was hilarious and horrifying to me that as soon as I'd gotten over the weird coincidence of Zach living with Sam's childhood best friend, the next two people I happen to meet and make dates with in New York City don't only know each other -- they were friends.

After I got back to my desk, I struggled to maintain myself while I explained to Hawaiian Shirt Dude that I did know his friend, but not because I'd ever taken a class from him... just simply because I'd met him that weekend at a bar. As if that wasn't ridiculous enough, I had to tell him that on top of that, the attractive yoga instructor was the reason I was going to be late for our date on Thursday.

Almost immediately after I'd sent that text message, I received another text. But, this one wasn't from Hawaiian Shirt Dude -- it was from the attractive yoga instructor, just stating "LOL heard you met my buddy [Hawaiian Shirt Dude]."

At this point, I couldn't handle life anymore and went into Chelsea's office to lay on her chair and discuss how it was remotely possible that without even meaning to, I was essentially two-timing these friends. (Working with my best friend has a lot of perks and having her readily available and within 500 feet of me at all times to deal with a crisis like this is definitely one of them).

After a long discussion with Chelsea and despite the (extremely weird) coincidence, I decided not to cancel either of my meetings with these two guys, mostly because a night spent with the combination of yoga and beer is actually my dream come true. It wasn't until Thursday, the day of the actual multiple dates came around when I finally realized this may be a bad idea. I came to this conclusion due to two reasons.

First, despite my ability to land myself in extremely awkward situations, I am very ill-equipped to actually handle them. And, second, when Hawaiian Shirt Dude text me that morning to tell me to say hi to his yoga instructing friend in class, I realized I was in way over my head because, not only am I not very good at dating, I am extremely unprepared to date two people at once, let alone the same day.

Also, I'd forgotten to account for how much I sweat during a Bikram class.

But, I showed up to the class. And, it went as well as it possibly could when the person you are interested in is teaching shirtless and you're sweating so much it actually looks like you fell in a small pond. 

After class had ended, we both had showered and I no longer looked as if I'd spent the last hour drowning, the yoga instructor and I walked out of the building together. We were chatting amicably by his bike when he put out his hand and asked me if I'd like to go grab a beer. And, in what had to have been one of the more uncomfortable phrases that have ever come out of my mouth, I had to say "Yes, definitely… but I'm about to go grab beers with [Hawaiian Shirt Dude]."

Still, I had about an hour before the date with his friend started and, even more so after taking his class, I was interested in getting to know him better, so the two of us sat on a bench outside the studio, eating grapes and talking about our lives. It was an incredibly enjoyable experience and not only because grapes are my third-favorite fruit -- I genuinely had a wonderful time learning about him and hearing his stories.

Then, he kissed me and I panicked.

To go off on a separate tangent for a minute, I want to point out it's very, very obvious my brothers and I are related. This is mostly because we look so much alike we're often asked if we're either some combination of twins or triplets and, in a few instances, Jonny and Dana have been mistaken for the exact same person. Despite our very similar physical appearance (height non-withstanding), the three of us are also quite alike when it comes to the way we behave and the decisions we make.

When I posted this photo on Facebook (with -- obviously --  a Kanye West lyric as the caption), my friend AJ commented on it and said we looked like an indie bluegrass band, which was maybe the third-best compliment we've gotten as a famil…

When I posted this photo on Facebook (with -- obviously --  a Kanye West lyric as the caption), my friend AJ commented on it and said we looked like an indie bluegrass band, which was maybe the third-best compliment we've gotten as a family. (Second place goes to when the bartender told Jonny and I we had the best eyebrows she'd ever seen on his 21st birthday and the overall ranking will always be when we were at a Louis C.K. show in Boston and someone looked at us, then said "That is the hippest family I have ever seen.")

Dana once told me a story about how, during his freshman year of college, he asked a girl to go to a concert with him, somehow forgot about it, asked another girl to go with him, then brought them both on the date.

Needless to say, it did not go well.

Despite being armed with this information, it was obvious I was my brother's sister when, immediately after the yoga instructor and I finished kissing on the park bench, I stood up, grabbed his hand and decided to take him on my date with his friend. At the time, this seemed like the best solution for the problem in which I'd found myself in. 

(Like I said, I'm ill-equipped for awkward situations).

Luckily, the universe realized how far in over my head I truly was. On our walk over to the bar to meet Hawaiian Shirt Dude, Hawaiian Shirt Dude text me, extremely apologetic, but canceling our plans because he had to work late. Which, really, thank God -- I probably would have spontaneously combusted in that awkward of a situation. And, so, I ended up completing my day of dates with my dream of yoga and beer… just with 1/2 of the correct people, but still having a lovely evening.

I never ended up going on a date with Hawaiian Shirt Dude. I couldn't. In the days following our original first (accidental) date, the yoga instructor had napped with me in Central Park and cooked dinner for me in my apartment -- after all of that, it would have felt too weird, too personal to go out with his friend. Besides, I was still trying to recover from the coincidental Sam situation -- throwing on another instance of dating friends in New York CIty just seemed like I was tempting fate too much.

Because, you know what? There are 8.4 million people who live in this place. And, you'd think that would give me some leeway, some reassurance perhaps that everyone I go out with won't know each other…

…But, apparently, it's just not enough people for me to date.