First Time For Everything

I messaged a dude a couple of days ago on OkCupid and then noticed that he kept looking at my profile but not writing back. So, I messaged him again and he finally responded saying that he wasn’t sure if I was out of his league (pshh sure) or not and he’s painfully shy. 

Well, that broke the ice and we chatted a bit, texted a bit, and then met up last night for a drink. He is a first year history professor at NYU and was quite sweet. He’s also divorced and has two kids (who live with his ex-wife in New England)! In all my years of dating (sometimes) older men, I’ve yet to ever encounter one who’s been through a divorce. He seemed rather matter-of-fact about it and not all that torn up; like it was just something that had to happen. Which is totally fine. 

I’m not sure if he was nervous or if we didn’t gel immediately. Not sure if I’ll see him again, but it was definitely stepping outside of my comfort zone. 


A few weeks back I was sitting by myself at the bar of a German restaurant near my apartment eating a burger. I apparently looked behind me, gave the person a look that said, “don’t talk to me” so of course he stepped right up and started talking to me. He asked for my number and I was so impressed with his brazen personality that I gave it to him. 

We went out twice. He’s not my type at all (and he admitted that I wasn’t his type either) and I was trying to give him (”it,” really, the time we were spending together) a chance – see if my type could change since I haven’t had much luck with my “type.” 

When I got these texts from him yesterday, I was stunned and also pissed. Being this decisive would probably be incredibly attractive if I was into the dude but since I wasn’t, this was just a text from a guy telling me that where to show up and what time and that he was taking me back to his apartment. Translation of this text: I don’t want to keep seeing you unless I know I’m going to get laid.

Well, douchebro, I don’t take orders. 

Hey, I tried. The spark just wasn’t there and unfortunately this dude didn’t know that demanding I go to his apartment wasn’t the way to find that out. On/up. 

Back on December 4th, I joined a march for Eric Garner and against police brutality. While we were stopped on the West Side Highway, I asked a dude what was being said or happening further away then I could see (he was tall). We continued chit chatting for a little while and then in the midst of a confrontation between police and protestors, we lost each other.

The following Saturday I decided to post on “Missed Connections,” fully expecting nothing. I wrote every piece of information that I could remember about him. A few days later, after I’d forgotten about the post, I got an email. It was him. His friend (who, he said, was the kind of person who spent free time reading Craigslist ads) had found it and forwarded it to him.

We met up a few days later after we both marched (separately) in the Millions March. It turns out that he was a fan of Buddhism and regular meditator. We also both loved John Lennon. And reading, among other things. It was really nice. It was easy. We meditated together. He met one of my best friends. He was completely honest with me about how he felt (and it was good) and I was with him too. I was pretty sure he was one of my soulmates.

Then he found out that he’d gotten accepted to a great school to go to their post-bac pre-med program and everything changed (understandably). He wasn’t a science person and he was trying to make himself one so he needed to study. And study, and study more. We decided last week when he came downtown to have lunch with me that it was for the best not to date anymore. He just didn’t have the time that he wished he had.

It was hard and it sucks. But it was also the logical decision. I still believe he was one of my soulmates, but as Elizabeth Gilbert points out above, it doesn’t always mean that’s the person you’re meant to be with.

I’m still trying to sort out what the lesson was that I was supposed to learn from these past two months. I’m sure it’ll come to me when I least expect it. Just like he did. 

How It Went: My Side


So, this happened. I’d kind of been in the pool of people they could pick from for a while but our schedules finally lined up and I said OK. At worst, it was a good story and free drinks. 

My words that were printed are accurate. I kept telling Dana, the editor, that there was no chemistry but he was a nice guy who just wasn’t right for me. I didn’t want to be portrayed like this asshole. Luckily, I don’t think I was. (But totally tell me if I was!)  And my side is only one side, but this is how the date went from my perspective:

I arrived at the restaurant and waited for a short while. He was about five minutes late – not awful. Like I said in the magazine, he seemed flustered and nervous. After he told the hostess who he was, I immediately introduced myself, we shook hands (or maybe we hugged? I don’t remember) and we were seated. 

I could tell sort of immediately by the silence that followed our being seated that I was going to need to lead the conversation. I had no interest in sitting in silence with a stranger. I knew he wasn’t my type when he appeared in the doorway all flustered and nervous (come on, this is a harmless date) and he didn’t look like my type physically but I thought, “he could be a really awesome person if we have stuff in common, let me dig." 

So, digging I went. I asked him what he did (publicist), where he lived (Astoria), what his favorites movies/TV shows/bands (Alkaline Trio was literally the only band he could name) were, I asked where he went to school, I asked him if he had pets, I asked what his hobbies outside of work were. 

Unfortunately, we had nothing in common. And I mean nothing. I had really hoped to find some sort of commonality to build a connection off of with him even though he wasn’t really my type physically. 

Awkward moments: There were more than one. (1) In the magazine I said he asked for a half-time report on how I thought the date was going (you’re 33, dude, if you have to ask, you know the answer isn’t good.), and when I answered honestly, he looked defeated. Sorry, dude, I’m not going to lie to you. (2) When we ordered drinks, I ordered some pink martini thing and he ordered a virgin bloody mary. I asked him if he was sober and told him that was totally cool if he was cool, but he just shook his head and said he wasn’t in the mood to drink. Well, whatever. I had two because conversation was pretty boring. (3) When he told me to stop asking questions and doing all the talking because he ”didn’t want a bad write up in the magazine.“ It became pretty apparently that he was worried about a bad write-up in the magazine more than actually getting to know the person sitting across from him. Also: when I stopped talking, he didn’t talk. So, I kept talking. (4) More than halfway through I realized I gave zero fucks about impressing this person because there was no chemistry. I may have been reading Kingdom Coming at the time so that’s possibly how we got on the topic of abortion and who should be deciding whether or not it’s legal. He thought the states should decide for themselves whether or not it’s legal. I told him that he was very entitled to his opinion but he was a dude, and has never and will never need to have an abortion, so I didn’t think he should have a say either way. 

Now I’m not sure how someone who works as a publicist and has to talk to people for a living is so bad conversationally, but he was probably just super nervous. He also had no confidence. After he answered questions a couple of times, he’d circle back and ask, "did my answer sound too unambitious/bad/whatever?” Dude, just be yourself.

He asked me to “make a pact” at the end of the date to not say anything negative in the magazine. What?! Like I said, he was only concerned with his write up. I said OK. 

Afterwards: After dinner he asked if I wanted to go to a bar (why, I thought, so you could not drink some more and we can continue this amazeballs conversation we’re having?!) and asked twice for my contact information. I declined all three of those requests as nicely as I could and went home, relieved it was over. 

I’m not big into wasting my time with someone that I can’t hold a conversation with on a date anymore. I have no problem saying to someone, “you’re really nice, but we have nothing to talk about,” and it was no different in this situation. 

This was really just a case of having no chemistry with someone. He’s not a bad person, just maybe slightly awkward. I’ve been told by a few dates/friends lately that I’m easy to talk to and that I have a “certain energy” abut me, so I’m not too worried about what this dude thought. He got rejected. I understand his hurt feelings.  

I’ve had people tell me since the magazine has come out that, “Look at him. Someone like you would never go for someone like him,” which they mean as a complement, but I feel like it’s kind of insulting. My attraction to someone is based more on personality than looks. I, of course, have a type, but it’s more than that. 

This was an interesting experience (I got what I thought I would: free drinks/appetizers and a good story!) that I’d never do again. Even though Time Out asks you a few questions about yourself, I don’t think they really work at trying to set people up who might be compatible. 


I was on the C train uptown tonight headed home after dinner with my best friend. A guy gets on at 72nd street and sits next to me with a huge stack of fashion magazines. He quickly looks at me and says, “These aren’t for me. My sisters cuts up magazines and when I saw these, I called her and she told me to take a few.” I responded accordingly (“ahhh.”) and then he looked at my jacket and pants, both of which were pink, and said, “You’re very pink today…. my favorite color is usually purple.” I told him that was my next favorite and he said, “What, after green?” With a huge I’m-Such-A-Witty-Nerd grin on his face.

I laughed and he asked if I lived in Harlem too, I said no and he said he lived by Columbia. I of course asked if he’d been to JOE on 120th and he said, “Nope, I’ve never been. Do you want to take me there? I’d like that.” He was totally not-creepy but still, I just smiled and thirty seconds later the train stopped at my stop.

I’ve never had an actual normal, sort-of-cute-in-that-nerdy-kind-of-way strike up a conversation with me on the train and it was kind of nice. I feel bad that I didn’t at least give him some kind of clue of how to find me, you know, Serendipity style.

Nice to know that nice (and seemingly normal) guys are still out there. 

Sometimes there’s a moment when you’re at a friend’s party and you see someone across a room who you might recognize but you don’t know from where. You exchange glances until one of you (him) breaks the silence and comes over to say hello. You talk for hours and when you decide to leave the party and there’s no paper to be found, he writes his number on your arm and, with pleading eyes, says you really have to call or text him. You both know that you have to see each other again.

And you do text him, the very next morning because why play games? He says he’s waiting for the bus and going back DC, where he lives. You text and talk daily for the next weeks and you somehow gather the courage to ask him to be your date to your girlfriend’s wedding, since he’d planned to come up the next day to hang out anyway. To your absolute shock he accepts, excitedly even.

He’s a wicked dancer and super personable. You’re totally impressed. You spend the weekend together, talking and getting to know one another. You eat pizza, drink wine, stroll through Central Park, watch an awful movie on Netflix.

Before he leaves he thanks you for a brilliant weekend, and for showing him a part of New York that he’d never seen before that he quite liked. As you watch him drive away, you smile and think how nice it was to get to know a new person and you admit that you might not see him again for a while. But you definitely enjoyed the escape from reality for the weekend.

Two Points For Honesty

Yesterday I did something for the first time and it was easy and felt great. I told a guy that I didn’t think a second date was a good idea because I didn’t feel much of a connection. He said, “okay, that’s fair,” and that was it. I didn’t have to make up any lame excuses. It was awesome.

A few months back I was seeing a guy who I thought was awesome. We had tons in common and I thought we clicked. Well he actually wasn’t so awesome because he didn’t have the balls to tell me that he didn’t feel a spark until three (3!) weeks after our seventh (7!) date in a month.

We had gone to see Guster together so he ended things with “two points for honesty?” I didn’t reply. And I defriended him on facebook.

As I just learned, it’s not incredibly difficult to be honest and that honesty doesn’t usually take weeks to come by.

for your saturday amusement

I had a falling out with a friend almost two years ago. He harassed one of my good friends and that wasn’t OK. So I called him out for it. He reacted in a less-than-mature way and I decided that a friendship with him wasn’t a good idea anymore. I told him that we weren’t friends anymore and to please not contact me. He’s refused to take the not-so-subtle hint and he has continued to text me every so often (as you can see by the time stamps). It’s funny. And a little sad.

I met this guy on OkCupid in 2009 too. 

the best guy ever

So the last person I’d started chatting with before I closed my OKCupid account was this dude. He’s a biochemist at New York Presbyterian and very cute. He was older and seemed sweet, but a little awkward. Then we texted too much, and I put off meeting him for too long (a couple of weeks). We finally spoke on the phone one night during which he ended up admitting that he does his best programming when he’s in a relationship because that’s when he’s happiest. Oh, and also that when he doesn’t have a girlfriend he’s constantly on the look out for one.

As awesome as a super codependent boyfriend sounds, I’ll pass. I told him a few days later that I didn’t think we should meet. He apparently thought I was joking though because a week (or so) went by with no communication and then he texted me out of the blue to tell me he was in some fly-over state for work. I had deleted his number (and texts) so I had no idea who it was. When I finally guessed correctly, he said he’d thought I’d been kidding when I said I didn’t want to meet and that I couldn’t possibly be that callous.  

I didn’t tell him that he seemed like an obvious codependent head case and that was why I didn’t want to meet him. I didn’t feel the need to pass judgment on him, and it wouldn’t help him anyways. Because really, who likes being told what their issues are? You need to sort that shit out yourself.

I just laughed when I got this last text from him though. I’m sure he is one of the best guys ever. That’s totally why he’s single. He’s too awesome.

Bullet: dodged. 

Bringing Out the Worst

I know people always say their significant other brings out the best in them and that’s great! But I didn’t know it was actual a thing to date someone who brought out the worst in you – or me, rather.

Remember the guy who liked to talk on the phone and who I had a semi-awful date with last week? He had all the best of intentions and was a genuinely sweet person, but he brought out the absolute worst in me. We had four or five dates and half of them started with him being unable to make plans, showing up late, and/or doing nothing but fighting with me.

This was how our final date went on Sunday. After the awful date last Saturday (which was in part due to the fact that I was in an awful mood, I get it), I took the initiative to make plans for Friday since I knew he was mostly unable to make plans in any timely manner. We were going to have a low key date, order in dinner, and hang at his place in Brooklyn. And I was kind of looking forward to it too.

I texted him on Thursday and asked what time I should show up in Brooklyn. He called and said he unexpectedly had some friends come into town but that he’d still love to get dinner and that he’d pick the place and plan everything. Awesome, I thought. When he called the next day and said he couldn’t find a suitable restaurant to go to in manhattan but that all his favorites were in Park Slope and his friends might be leaving that night anyway. So I should come out to Brooklyn. This was at 8:30pm. Nope. I said lets get dinner but I’d made plans for Saturday morning with my friend that was staying with me. He said he’d come uptown. I told him a place and he said it’d take too long to get that far uptown and he wasn’t even hungry and wasn’t planning in eating anyway. So he’d just sit with me while I ate.

Uh, no.

For some reason we rescheduled for Sunday in his ‘hood for brunch. He picked the place and he texted me at 12:15am on Saturday night but I was already asleep so I responded to him on Sunday and he told me where the place and I went to meet him. One o’clock rolled around and I exited the F train and called him. He said he still hadnt showered but to come to his place and I could hang out while he got ready.

No, no, no. We’d decided on 1pm-ish and I was famished and exhausted. He quickly dressed and met me. I almost walked away before we got to the restaurant because he was being blatantly disagreeable with me but he begged me to have brunch. We walked to the place, put our names on the list, and walked up 5th avenue. I bought an adorable ring for $2.75 at Housing Works and we explored a bunch of other cute stores.

We were called back and seated at the restaurant and had brunch. We talked the entire time about how we had nothing in common (but, he pointed out, we were both human beings – well if that’s all it takes, let me just date everyone!), he hated how his food came out after he’d put in a very specific order, and then the rest of the time we quietly argued about our blatantly obvious differences.

When I said afterward that I didn’t see this going anywhere and that I thought it’d be best if I went home he was livid. I’d been expressing the entire afternoon how I didn’t think we were compatible but he just pressed on.

I had to cut it off though. I left, feeling badly if I’d hurt him, but mostly relieved because it was frustrating being around him. It felt like babysitting. I’d told him I’d dated guys like him before to which he responded, and I quote, “Uh no, I can tell you for sure that you’ve never dated anyone like me!

Well, okay

And I decided I wanted to keep it that way too.