—Sunday, May 27, 2012—
This was a tricky one. I worked in an office with so few single women that I may have literally had two people to choose from when initially attempting this date. I had looked to our Boston headquarters for options too, but that hadn’t panned out. The project was winding down and I needed a miracle.
At the start of my day, I was really unsure of how to dress for this date. It was hot in my apartment and I knew it was warm outside, but we’d likely be out for a while and it was possibly going to rain, so it was apt to cool down. Man this was hard.
Shorts? Yeah, fine — let’s go with shorts. A t-shirt?! Maybe. I put on a v-neck t and I thought I looked good. Really, I thought it looked great. But I also understood how a t-shirt could give the impression that I was not trying. I cleaned up a pair of Top-Siders which I figured would save the outfit from looking lazy. Overall, it was very casual, but I knew I looked attractive. I just didn’t want Tessa to think that I wasn’t trying. If only she knew how much stress this wardrobe decision had caused me.
The other thing I considered was that Tessa saw me in a collared shirt every single day at work. She sat right next to me, after all. I figured that I might as well be as different as possible from my work self. Who knew? It was possible she would never see me in this light again.
Tessa had worked with me, on my team, for almost a year by the time of our date. We sat next to each other for the first few months, then apart, then back together. I could remember when she first started. As I stood to greet Tessa on her very first day, I received an email from Co-worker Brad that just said, “Calm down.”
He had a point. Tessa was really quite good looking. As I came to find out, she was also super smart and very nice. She was awesome, basically. However, she also had a live-in boyfriend. Hence, she was not among the few available women in the office. If she had been, I wouldn’t of thought twice about who to ask on this date.
But then, a miracle. One day at work, less than two weeks before our date, she leaned over from her desk to show me a funny email she’d received the great folks at OkCupid. Apparently, she was on OkCupid. The gears in my head fired up and I put the pieces together, eventually asking her what had happened.
As it turned out, she and her long-time boyfriend were about three weeks removed from each other at that point. Recognizing that Tessa was not only one of my few options for a co-worker date, but also the ideal one, I sent her a very long and carefully worded email that Saturday morning, asking her to go on a date with me. I was extremely nervous about it. I mean, I didn’t know how it would be received. We worked in a fairly corporate setting, so it was was not as carefree and friendly as asking out a fellow server or something. Also, we sat next to each other and collaborated frequently.
But as you probably figured, she said yes. When I read her reply, I was so pumped. And I was still so pumped on the day of our date. Tessa was totally someone I wanted to go out regardless of the project, so she really was the ideal co-worker date.
Heading out from my apartment, I just hoped she hadn’t dressed way better than me. Whatever though — it was Sunday and we were going out in Brooklyn. I was wearing a v-neck t-shirt, which was the equivalent of All-Access VIP pass to White Brooklyn.
I waited for Tessa in Greenpoint by the Nassau Avenue stop on the G train. We were going to this place Do or Dine in Bed-Stuy, so the G was our ride. I had offered to stop off in North Brooklyn to “pick her up” and she was letting me do so. She texted me to say she was running just a little bit late, but that was fine. I was passing time by texting with the aforementioned co-worker of ours, Bradley. [You may remember him from Double Date.]
After not too long, Tessa appeared across the street in a very weather-appropriate paisley sort of dress. She looked really nice and less importantly, I didn’t feel underdressed. As I crossed the street on a green light, Tessa took a few steps out to greet me with a hug. I was worried that we were in the middle of the road, but luckily there were no cars coming.
This friendly hug was the most physical contact that Tessa and I had ever had at that point in our relationship. It was almost bizarre to think that I had been in close proximity to her day in and day out and I had never hugged her. I guess that was normal for co-workers, but my other “co-workers” were improvisers and those people hugged all the damn time. Either way, I was happy that it had finally happened and was looking forward to at least one more by the end of the night.
Apologizing for her tardiness, Tessa told me she was late because her little pup Zooey had required a cold press to help deal with an infection. I didn’t really know what a cold press was, but the situation sounded sad and kind of intense. Yes, she confirmed, it was sad, but she wanted Zooey to be healthy, so she’d do whatever it took. That made sense to me.
We went down to the G train platform and waited for the train. It took a few minutes but we eventually set eyes on the allusive G train which would take us to points south. Tessa told me about that morning’s brunch adventure and we talked about transit between the boroughs a bit, and the different neighborhoods of Brooklyn and Queens. She was impressed with my knowledge of the G train, presumably because no one gave a damn about the G train. My affinity for it made sense though, since it was the only train link between Queens and Brooklyn. As such, I’d been on it a number of times. Also, I looked at GoogleMaps a lot while at work.
Tessa had suggested the restaurant, Do or Dine, which was supposed to be a pretty hip spot to eat in the ever-changing neighborhood of Bed-Stuy. I wasn’t surprised that Tessa had come through with such a great recommendation, as she was a bit of a food nut. I don’t mean this merely in the way of consumption either. Tessa cooked a great deal and frequently baked delicious treats to share with her co-workers, which we all loved and appreciated. Anyway, I had looked up Do or Dine and it had a very tongue-in-cheek kind of menu that looks fabulous, so I was excited for it.
We got off the train at Bedford-Nostrand Ave and the station was huge. We were trying to figure out which way to go, wondering aloud, when a woman pointed us in the correct direction. “If you go that way [pointing the opposite direction], you’ll be in the middle of nothing,” she told us. Thanks, lady! Clearly, we looked like lost visitors in a strange land.
Once above ground, I used my phone to orient us and proclaimed that GoogleMaps was great. Tessa then said that she loved maps and that she looked at GoogleMaps more than anyone, but I challenged her on this. That was why I knew where so much shit in NYC was located without ever going there — I just stared at GoogleMaps all day sometimes. I also told her how fun it was to fly Virgin America out of Boston because their headrest screens had GoogleMaps installed and I could look out the window upon Eastern Massachusetts and line up things I recognized with the map. It was was like real-life satellite view.
Do or Dine had an old West Indies restaurant awning still hanging outside of it, but “Do or Dine” was painted on the partially pulled down security grate. You had to get all the way up to it before you could confirm it was the right place.
It definitely had a cool vibe as soon as we walked in and very few patrons that day. I seemed to recall that someone from the restaurant had been on Food Network’s “The Next Food Network Star,” or something like that. I’d thought I had seen it on their Facebook page and Tessa said that it sounded familiar. It was supposed to be a bit of a destination in the neighborhood, so it would make sense if there was some kind of fame attached to it.
We chose to sit outside and grabbed the end seats of a big long picnic table. There were a couple other parties out there, but that was it. We were given menus and left to look them over.
There must have been a mistake though, because we seemed to be looking at brunch menus. It was almost 7 p.m., but as we were informed, this was intentional. We asked the busboy and the server and they both assured us that Do or Dine served brunch all day and night on Sundays. Even on holiday weekend Sundays. It didn’t matter than the next day was Memorial Day.
We were not to receive dinner menus, and while that was somewhat disappointing, I was sure that the brunch menu would still be good. I just knew that Tessa was really looking forward to eating there and I felt bad that we were not getting the full menu.
Still, our options looked really good. We discussed cocktails first and then food. I stuck to light and citrusy while Tessa went with something whiskey based. Opposites attract, guys. As presumed, the menu was quite quirky with funny names abound. It was exactly the type of place that the Fuds Menu people were trying to mock at GoogaMooga the previous weekend. God, that thing was so funny.
We saw the “fish and chips” come out to another table and while I was already leaning towards ordering it, the visual solidified my decision. It was a whole flash fried red snapper on a pile of frites. It looked awesome. Tessa decided to go with the “chicken and woffals,” although it was definitely outside of her then paleo diet.
I had been trying to keep that diet in mind when planning this date, and knew some details about it, but used this as an opportunity to ask Tessa exactly how it worked. She told me that there was a list of things she couldn’t eat, namely wheat, legumes, sugars and maybe certain oils. Definitely not anything fried. She said that it had been pretty easy to stick to and that she felt better overall since starting it. That was cool — I thought it sounded like a good thing that I would actually consider doing.
She also added that she was not too strict with it though. For instance, if she was coming to a place like this, where she’d been wanting to go for some time, and there were no good paleo options, she would just cheat. She was doing the paleo thing with another co-worker and she said that he cheated all the time, but even still, he’d lost something like 15 pounds that month, which was pretty impressive regardless.
There was a French family seated near us and I wondered how such a group came to be at a restaurant in Bed-Stuy, Brooklyn. It wasn’t exactly a tourist-destination. In fact, it was far from it. I didn’t know, but there they were, adding to the ambiance.
Our drinks came out, but Tessa’s initially had a bug in it and the waitress was super passive aggressive about it. Chill out, lady. We had also ordered the foie-gras doughnut to start and that came out quickly as well. My assessment of the savory treat was that it tasted really weird. It was literally a hot jelly donut with chilled foie-gras also piped in. Tessa liked it while I was indifferent, but then again, she really enjoyed foie-gras. It tasted good but the whole thing was a little much for me. I was definitely happy that we had tried it though.
As one might expect, we talked a lot about work over the course of our meal. Tessa had only ever worked in our NYC office and had been there less than a year, so she didn’t know the history that a number of us had together. I told her a little about the group of roughly eight guys who had all worked in Boston together doing quality assurance and then, one by one, moved on to NYC consulting. I told her who had lived with who and some of the other micro-factions therein.
She loved hearing about this stuff. It was almost like non-detrimental gossip. I think Tessa found it interesting to hear about all these people she worked with every day, but hadn’t really gotten to know yet.
I also went on to tell her about how I considered co-workers Brad and Phil to be very close friends of mine. They were both so great, but so different at times too. The three of us were a dynamic bunch for three dudes that worked in financial software consulting. Tessa thought Brad was hilarious and I had no choice but to agree with her. He was a riot.
Our food was really delicious. There was no way I could eat all of my frites but Tessa helped out a little bit. We both had a taste of the other’s dish and it was nice to collaborate on sharing a meal rather than completing a spreadsheet for once.
In addition to work, we also talked a little bit about the project. Tessa wondered if I was going to be bored once it was all over, but I assured her that there was no time for boredom. I knew full well that improv would simply pick up the slack, not to mention all of the general life things that I’d been ignoring for the past year in NYC.
We discussed her snobby (Yet lovable) Manhattan friends who always wanted to take cabs everywhere and how it was hard to get them to go to Brooklyn even though she lived in Williamsburg, the hippest of neighborhoods, and was close to the train. I talked about my roommate Pat and how I knew him through my other friend Tony. I then described the network of friends that I had in NYC from Fairfield and how a bunch of them also did improv. I’d always had friends to look up to who were both corporate professionals and improvisors.
Overall, it was a great meal and we sat for a bit as the sun disappeared behind the adjacent buildings. We split the bill even though I joked with Tessa that I made way more money than her, which was not true because we had the exact same job.
We both used the bathroom on our way out and I saw a little postcard for the Next Food Network Star, so it seemed like our suspicions had been correct. We walked down the street, back towards the train and we came across a couple in a yelling match outside of a laundromat. Tessa worried that the couple was yelling in front of their children, setting a bad example, and told me that she sometimes caught herself swearing in front of her dog and would then realize how dumb of a concern that was.
Actually, I had noticed over the course of the date that Tessa swore a pretty good amount. I mean, she swore as much as I did, but it was interesting because she was so quiet and soft spoken at work. I liked this side of Tessa. She also had a really good sense of humor. She was frank and had a bit of a mouth on her. I was a fan.
Down on the train platform, Tessa remarked on how the place was deserted. It looked like we had just missed a train. I talked about how people were really scared to jump down on train tracks, but relative to other things, it was really not a big deal. I don’t know what I compared it to, but hopefully nothing that made me sound stupid. We also discussed terrorism and talked about how the security at the New Orleans airport, where we’d both been somewhat recently, was really nice and stress-free. Fortunately, it was actually not very long before another train appeared.
We were only traveling a few stops away, back to Williamsburg, to try and catch a 9 p.m. show that Hannibal Buress hosted at the Knitting Factory. On our way out of the subway station, I told Tessa that I liked her dress. Then I told her about how worried I had been when getting dressed for this thing. She laughed at me.
Unfortunately, we didn’t get to the Knitting Factory until 9:15 p.m. and they were at capacity with a line outside. We stood in line for just a couple minutes before deciding to go get drinks elsewhere. I pulled out a little piece of paper with a few places on it that I had looked up previously. I asked Tessa if she’d been to any of them and we chose one that she hadn’t been to before.
And with that, let’s pause for a tangent of dating advice. Having a little piece of paper with you for notes is actually a good move. Maybe it wasn’t so slick in the way that had just used it, but I had also used it earlier to confirm the address of the restaurant and Tessa hadn’t even seen me pull it out. If you just write down a few things, like maybe a name, time or address, you can easily glance at it later. Sure, you could store this kind of information on your phone, but as soon as you look down at that little screen, your date’s first assumption is that you’re communicating with another person or using social media. Both of those things are poor form while on a date. However, if you jot your notes down on a piece of paper, it’s much less intrusive and it looks like you did your homework. Dates appreciate that.
Leaving the line at the Knitting Factory, we headed to Kinfolk Studios. It was supposed to be aggressively trendy and as we arrived, Tessa recognized the place. There was a dinner that was hosted there once a week and she’d been trying to get reservations for months. That night, they had a DJ cranking tunes, a garage door open to the street, numerous attractive people and the music was loud. Seemed trendy enough.
We both ordered the same rum-based drink and found a table in the back, where no one was hanging out. Cheers.
Given recent happenings in Tessa’s life, we talked about break ups and how it was never easy, even when it felt right in the end. She said that she was sad about her recent relationship ending, but ultimately very happy that it had happened. Often times, people stayed together much longer than they really wanted to just so they could avoid the sadness of the breakup they knew they needed.
I related to Tessa the drawn out relationships that I’d had with my first two girlfriends and she admitted that she’d been thinking about hers for a while as well. Then, just like that, it was done with and now life was better. We talked about my last relationship a bit and how that had been tough for me. I was jealous so much in that relationship and things had felt unfair. It had hurt a lot. I told her that Phil and Brad had to deal with me throughout that entire time and that they were great supports. Tessa thought it was funny that I’d gone from never being a jealous boyfriend in my previous relationships to being very jealous in another and we talked about maybe why that had happened. She also asked how Phil had met his girlfriend Monica.
I probably wasn’t at privilege to tell her this, but I knew Tessa could be trusted. Monica and Phil had known each other from working together but only began dating after Phil’s long-time girlfriend, his high-school sweetheart, had passed away. The tragedy, and recovery from it, had bonded them. I was near tears as I recounted the story and I could see Tessa’s eyes well up too. It was just so tragic. It really was. Earlier, I had been telling Tessa how Phil was busy all the time and let her know that some of those times, like the current weekend, his schedule was filled with something related to his late girlfriend. It was a very emotional talk, but Tessa was impressed to know that Phil had dealt with so much and was still the cheery person she knew him to be. There was so much we didn’t know about those around us. It was really true. Always is.
Lightening the mood, Tessa asked me about my LARP Date the night before and then about other interesting dates I’d been on recently. I told her about Married Woman Date and she asked how it was. I told her that it was good and we talked about open marriages and relationships a bit. She didn’t think she could do something like that as managing the jealousy seemed difficult. I talked about certain things I’d read in “The Monogamy Gap” and it was a decent conversation, but I wasn’t going to convince her of anything. She was open minded when it came to other people, but she didn’t think it would work for her.
She asked if I wanted to go somewhere else, and that sounded good to me. I closed my tab very slowly, thanks to the top notch service at the bar, and we headed out.
Tessa led us a few blocks away to Hotel Delmano, a cool looking cocktail joint on Berry Street. She liked this place, she told me, and it was evident why as soon as we stepped inside. Everything was so well put together and had a sense of authenticity that other cocktail bars lacked. There was a rolling library ladder behind the bar which allowed access to the top shelf booze. It was probably just for show and Tessa confirmed that she’d never seen anyone on it, but it was cool looking.
Our host was a curious man who seated us after only a minute or two of waiting. Tessa said that she was sitting in the exact same seat as the last time she’d been there, which was a fun coincidence. We discussed drinks and each placed our orders. I’d had my fair share of cocktails so far that night, but I liked it. I felt classy.
Waiting for our drinks, we talked more about some of the dynamics around our office and the company. We wondered about some of the office romances that existed and the private lives of some of our more reserved co-workers. It was funny to think about certain people flirting or being romantic, mostly because we never got to see that side of them in the office.
Getting into career stuff, I confessed how I didn’t really want to be working at our company any longer and how I had checked out a while ago. Tessa liked the job and the company so far, and even talked about opportunities she saw for advancement. I was pretty pessimistic about it, but I tried to tell her that I was also more jaded. Plus, we had different priorities. I wasn’t as concerned with financial stability as she was, though I could definitely understand the desire. Truth be told, that stability was a big reason I hadn’t left yet.
It was an interesting conversation to have with a co-worker, about how I didn’t give a damn, but I’d already had it so many times with the guys, it didn’t seem out of the ordinary. I mean, who really wanted to be working in investment technology?
I used the bathroom and upon my return, I asked Tessa about all the places she’d lived in her life, since I knew there had been a few. Her father was a professor and because of that, they had moved a lot. Tessa was born in China, moved to Scotland, then Northern Australia, onto Melbourne, back to China for a year to relearn Chinese, then Colorado, Vermont and finally, New York. [I may have missed one locale, but most of it was when she was a little kid, so it couldn’t have mattered too much.]
She told me a bit about her mom and how she was very critical of Tessa’s choice in men. She’d gone on a date recently with a Chinese guy and her mom was very happy about it, but Tessa told me that she wasn’t generally into Chinese men. She said she either found them unattractive or they had over-inflated egos because so many women liked them if they were super attractive.
We talked about race in dating, work and improv. It was not too dissimilar to some of the conversation I’d had with Lisa the previous night. As a white man, I was simply unaware of a lot of things, unfortunately. Specifically, we talked about how it was hard to know when we were crossing the line with Asians. With blacks, for instance, it seemed like any joke at their expense was over the line, and understandably so.
But Asians themselves seemed to joke about their culture so much with us white folks that it was hard to tell where the line was sometimes. Tessa agreed and she hated that it was so accepted on both sides of the equation. For example, the wave of recent Jeremy Lin headlines were largely quite offensive. So many of the headlines and articles had been just plain racist, she said, but people only called it out when it was way over the line. And amongst it all, the Chinese community mostly encouraged the fanfare because of the excitement that surrounded him, rather than calling out the media outlets for being insensitive. It was a weird time.
With all the racial talk in the air, I mentioned to Tessa that she was my first Asian date ever. The closest I’d come previously was half. “Oh, yeah,” she said, “half-Taiwanese and half-Hatian.” Tessa had read that date before and remembered being annoyed that the girl wouldn’t eat dumplings at the restaurant because her grandma’s were so much better. Tessa understood that attitude of superiority — because her mom’s dumplings were clearly the best — but that didn’t prevent her from enjoying other great dumplings. That girl was dumb, Tessa concluded. I laughed, loving this straightforward side of Tessa that I hadn’t seen much of at work.
It took a while for our second round to arrive — we nearly paid and left — but then our waitress finally showed up with our drinks.
For whatever reason, I decided to bring us back to a discussion on monogamy and this was where things got a little hairy. Tessa was fairly traditional in the sense that she thought that love and sexual fulfillment should probably coincide. She didn’t claim that they did for everyone, but for her that was the case and that was what she sought out. Partners should be up for anything but if something didn’t work, the person asking needed to just accept that and not push it further. I was probably harping on Dan Savage’s GGG theory and I argued a little too much with her.
I knew that I wasn’t winning her over and I tried to clarify that I didn’t think anything I was espousing was absolute, but I did find it incredibly fascinating. I admitted that when the whole OHD dates thing was over, I very well may go right back to being a serial monogamist. I really didn’t know.
Fortunately, we got off of the subject before using the bathroom again and deciding to leave. I sneakily paid the bill while Tessa was in the water closest and we left around 1 a.m.
Walking south down Berry, Tessa asked me how I was getting home. I wasn’t sure, but if I was close to the L, then that, or the maybe the G. Perhaps I’d even treat myself to a cab for the second night in a row, but they weren’t particularly easy to find. Either way, I would walk her to her front door.
Tessa seemed to live in a really cool building in an amazing location, but I’d have to wait some time before I ever saw the inside of it. For the time being, I gave her a hug and thanked her for a wonderful evening. She reciprocated and I told her goodnight.
“See you Tuesday!” she said as I stepped away from her building.
Yep. I’d see her Tuesday, back at work, where our dynamic would return to normal.
At Bedford Avenue, I stuck my arm out and grabbed a cab home. Thank heavens.
**FUN UPDATE** About a year after this date, Tessa began dating none other than Co-worker Brad. It was a nice little cap to this story since the two of them were the only two co-workers I took on dates. If you’ll remember, Bradley was my partner in crime on Date#67: Double Date and plus, he’d been mentioned on this blog more than any other co-worker. It was only fitting that the two of them ended up together. Hurrah!