Wedding Date

—Saturday, July 9, 2011—

I could not figure out how to start the fucking Prius.

It was 6:30 a.m. on a Saturday and I had barely slept. I had to be at a wedding in upstate New York in less than four hours.

I needed the car to start.

Fifteen agonizing minutes and a call from the car company’s service people got the vehicle started and I was on my way, roughly 45 minutes behind schedule, but since I had planned on being there early, I was still in the clear. I’d be there on time for the ceremony.

This was the day that I attended a wedding with complete strangers—my date included.

Stefanie had sent me an email the day that One Hundred Dates went live in June 2011. She explained to me that she had a wedding to attend during the second weekend of July and wanted to know if I would consider being her date. One of the bigger dates on my list had landed in my lap. I knew right then that there was no way I could pass on the opportunity.

I was driving north from New York City, making sure I did not do anything stupid. My driving experience in and around NYC was sparse and often filled with confusion. I made it over the George Washington Bridge, into New Jersey, and…

“Fuck.” I missed my first exit. No matter, nothing that couldn’t be made up for with some strategic speeding. Reroute.

Drive, drive, drive drive drive.

“Fuck.” I really wish that state trooper hadn’t pulled me over.

I was two hours from home, a little ways north of Poughkeepsie, and only a couple minutes prior, it had seemed to be the perfect time for the strategic speeding previously discussed. At least the officer was extremely kind as he handed me the ticket. I turned back onto the road and kept the speed to a minimum.

Drive, drive, drive drive drive.

“Fuck.” I drove right past my exit towards Albany. What was going on with me that day? I had never before had so many things go wrong on any drive in my entire life. Reroute.

Drive, drive, drive drive drive.

“Fuck.” I drove past the church. To be clear, it was the only church on the road and there were people gathering outside. You’d think that would have been a tough thing to miss.

I parked. I was there. I was 30 minutes early. Go figure.


It was one of the most beautiful days anyone could ever wish to be married on. The sun was shining bright in the late morning sky as everyone arrived. The small chapel and the town of Fort Edward which surrounded it reminded me very much of my many trips to Vermont, where my father grew up.

I was waiting in the church’s driveway, occasionally checking my phone and otherwise attempting to look comfortable standing in isolation while strangers reunited with old friends and family. I was noticeably nervous. After about 25 minutes of this, we were ushered inside, where I found a seat by a window with a largely obscured view of the alter. Ironically, I chose to stay in the inconvenient seat, figuring that I must have been the least significant person there and if someone had to sit there, it might as well be me.

Then, through the window to my left, I saw the bridal party pass by as they prepared to enter the chapel’s front doors. This was the first time I saw Stefanie. She immediately stood out as the most unique bridesmaid with her red hair and blue/green framed glasses. In seeing her, my nerves settled a bit and felt a little more at ease. At least I knew I was at the right wedding. Furthermore, she was cute. In my mind, I high-fived Andrew WK.

The ceremony began, and when the bridal party entered, I made eye contact with Stefanie and got a small wave hello. It was a beautiful ceremony. The reverend had known the bride since birth and apart from his pride, he was also filled with humor. The ceremony was simultaneously precious and lighthearted. This was exemplified when a young baby cried out after the reverend finished his “speak now or forever hold your peace” bit. It got a good chuckle from the congregation. Everyone was in love with the couple, almost as much as they were in love with each other. It was truly a thing to behold.

After a creative and uplifting homily relating the needs of the characters in The Wizard of Oz to the needs of a marriage—Courage, Brains, and Heart—the couple donned their tri-toned wooden wedding bands and sealed the deal with a kiss. They were officially husband and wife, and there was much rejoicing.

It was time for the most nerve-racking part of my day.

I exited the chapel to greet the receiving line, where I was about to meet Stefanie for the first time. I approached, one handshake at a time, until we were face to face. She gave me a big hug and briefly introduced me to the rest of the line, but in the interest of traffic flow, I continued on. I was almost as nervous when I arrived in front of the bride and groom. These two were sharing one of the most momentous days of their lives with me. I did not feel quite worthy of the honor, but they were quick to make it clear that I was welcome.


After many photos and a bit of a drive, we arrived at the reception hall in Saratoga Springs. Stefanie was whisked off to the VIP room, so it was up to me to seat myself. I grabbed our name card and headed in search of Table Ten.

Fully aware that no one at the table had any idea who I was, I introduced myself before sitting down. I slid into the chair next to Kris, who immediately warned me that while I was free to sit there, his girlfriend would likely give me the boot when she arrived. I thanked him for not letting it come to that and I moved one seat to the left. I spent the next 30 or 40 minutes talking with Kris, whose girlfriend Amanda was a fellow bridesmaid, and Midge, whose boyfriend Rob was a groomsman. The three of them were living it up in the Champagne Room while their dates made nice with each other at Table Ten.


I returned from the bathroom to see the table filled out by Rob and Amanda and I saw Stefanie’s things at her seat. I’d missed her arrival. Oh, the suspense! But then she approached the table, mimosa in hand. She reintroduced me to the table, not realizing how good of a job I had already done of it. I could quickly tell that we were going to get along. She was funny, friendly and forthright. The three F’s, which I have just invented. The day had been considerably awkward thus far, so her arrival and conversation was a welcome change to my comfort level. I felt good. My anxieties withdrew.

Brunch was served. According to Stefanie, this was one of the main reasons for having a morning wedding. The bride was a huge fan of brunch, as was Stefanie. I have been known to have strong opinions on brunch, in that I think it’s kind of bullshit. Brunch is a word created by a group of twenty-something women in Manhattan to be used as an excuse to sleep in late and drink alcohol with breakfast, or alternately, to lessen the guilt associated with getting out of bed at lunch time. For the sake of this wedding though, and because there was a personalized omelette station, I was totally down with brunch.

As the reception progressed, brunch ended, speeches were made and personalities began to present themselves. Stefanie and I were certainly getting to know one another, but it did not resemble the typical job interview associated with first dates. It felt much more like two distanced friends playing catch up. Our private conversations were intermingled with the group dialog of the table and interrupted by the occasional visitor. It was an effortless approach and I enjoyed myself a great deal.

Then…TIME TO DANCE! What’s my favorite part of a wedding? Wearing a suit. My second favorite part? Dancing in said suit. Most of Stefanie’s friends had already been out there on the dance floor for a few songs as we joined the crowd. Some of them were really cutting a rug, but the dancing was mostly quite silly and very casual. After all, it was only about 2 p.m. and the open bar was still young. It would have been odd if people had gotten hot and heavy at that point, but then again that would probably be out of line for a wedding in general.

More drinks. More dancing.

A pair of Stefanie’s girlfriends told me they were impressed with how well I was doing. I had been given some warnings from Stefanie that her friends were rather forward and potentially a little crazy, but at that point, I just thought they were all great. Sure, they may have been quirky and different, but most groups of friends are like that when you get down to it. I was not finding it difficult to be an outsider in the least. In fact, there was an advantage to having so few know my name—I was never called out into the middle of the dance circles. Thank goodness too, because I didn’t want to show everyone up.

After the trio of Hall & Oates, Prince and Footloose, I was sweating my proverbial nuts off and headed to the bathroom to cool down. I returned to Table Ten, where Stefanie was waiting for me. The music paused and then began again quietly. Willie Nelson has written some beautiful songs, and Always On My Mind is one of my favorites. On the way to the dance floor for our only slow dance of the afternoon, I told Stefanie for the first time how nice I thought she looked.

I often find compliments difficult to give, and when I was only just starting this project, that hesitance was quite pronounced. Everyone likes being told they look good, but I have trouble gauging whether women view this as the kind flattery it is meant to be, or as a less-than-subtle way of saying, “I want to be inside you.” I regularly fear that they will assume the latter.

Stefanie took the compliment in stride just as I had hoped she would. My arm wrapped around her waist and I held her right hand in my left as we began to dance. Besides the mildly awkward hug we had in the receiving line, this was the first real physical contact Stef and I had had all day. It was pleasant, not stiff, and there was something reassuring about it. She was not someone who was afraid of me. She was not someone I needed to be nervous around. Something about it told me that I had already gained a new friend.

The dancing ultimately died down as the reception itself ended around 5 p.m. and the various parties peeled off to check into their hotel rooms there at the inn. Stef’s suite had a high-ceilinged living room with a bedroom loft overlooking it. It was a huge room and considering the large number of people who had not booked anything, it certainly seemed like it would be the evening’s homeless shelter.

After a quick change of clothes, we found our way downtown to The Saratoga City Tavern not long after 6 p.m. We ordered our drinks and I put Stef’s cider on my tab. I found it interesting that after spending roughly six hours together, the drink was only the second or third thing I had done that was indicative of being on a date with her. It made me feel good. Not because I was paying for her, but because I finally felt like I was doing something for her rather than simply tagging along with her. We took the elevator up to the fifth floor roof deck where everyone was hanging out and talking.

Before too long, I found that Stef and I had branched off from the rest of the party. We both leaned against a wall in the cover of the shade while most the wedding party enjoyed the sunnier and more lively side of the roof deck. Our conversation became a bit more personal. We talked about our families and our past relationships. We got candid. It was reassuring not to feel as though I needed to impress her. Slowly, more and more people filled the roof deck, including a very entitled bachelorette and her swarm of lady friends.

The sun began to set and the drinks continued as Stef and I talked over the next couple hours. Beers for me, 7&7‘s for her. Another bachelorette party came storming through. In time, we rejoined the rest of the wedding party. Her friends were fun. I was having a great night hanging out with them. No one made me feel unwanted. They were a good cast of characters: the gay, the lush, the goof, the tough guy, the Ferris and many more. While they were all unique, they were also an incredible singular unit when put together. Similar to the Power Rangers, I suppose.

As we seemed to be nearing the end of our night, sleeping arrangements were discussed, and being that I’d been in and out of buzzed and drunk since 2 p.m., I leaned in and casually asked Stef if I would maybe be able to get a slice of that king sized bed in her room. Just a slice. Just a sliver. She quickly assured me that it was her room, so of course her guest would get to share the bed. Let the foolish boys who failed to make plans sleep on the ground.

At one point, I thought we were leaving, but no one else came outside with me. As I waited, I saw at least two or three bachelorette parties pass me by. I guess it really was wedding season. The executive decision was then made to stay there for a little while longer and dance. The fourth floor was our destination, and as we made our way to the front of the room, we settled in between, I shit you not, two more bachelorette parties. Saratoga Springs must have been the only place for miles and miles for people to celebrate marriages.

Finally, I was dancing with Stef and not next to Stef. As I stepped away for a hot second, I was tapped on the back by a cute blonde girl in one of the bachelorette parties. Her eyes were a little glossy from what I could only assume had been a cocktail-filled evening, complete with penis straws. What was immediately apparent was that she was a terrible dancer. I was doing my best, but there was no telling as to where she was going next. I spotted Stef and gave her a look that said, “Save me.” She held up her glass of water, offering it to me. Yes! Team Teamwork! I politely excused myself and went to Stef. I took the water from her, thanked her and she and I returned to dancing.

Eventually, I was sucked into the middle of the other bachelorette party flanking us as two women began to dance with me. Apparently, my faux-dance moves were quite intoxicating. Or maybe it was just the booze? We will never know. I was impressed by how attractive and well dressed both of those young women were and that they wanted to be dancing with me. I ditched them quickly to be back with Stef, but as we prepared to leave several minutes later, I drifted over to say goodbye.

What was that they said to me? I was the best male dancer in the place? My ego inflated ten times. For anyone who knows my deepest darkest secrets, they know that I love to dance, so this was awesome news. Furthermore, I couldn’t believe I was being singled out by those women. Simply by the way they looked, I knew those women would never talk to me in Manhattan. I highly suggest that all my single male friends go to Saratoga Springs in the summer. You will feel popular.

We stumbled out into the bachelorette party parade that was Caroline Street and found our way into a pair of taxis that ushered us back to the inn. Once inside, amongst the Michelobe Ultras and Corona Lights that were passed around, a game of truth or dare began. After a number of turns, someone was finally brave enough to go after the stranger in the room. I got the sense that if I chose dare, I would be made to kiss Stef. With that in mind, I chose dare. There was no kiss though.

Instead, Stef and I had to switch clothes. We got down to our skivvies right there in front of everyone and exchanged wardrobes. There was a moment where I became incredibly worried that Stef might not fit into my pants. I am very skinny, with zero hips, and I frequently meet perfectly fit women who tell me that they would not fit intro my pants. In fact, my last girlfriend demanded that we try on each others’ pants so that she could know, conclusively, if she was larger than me. I breathed a sigh of relief when Stef hiked them up and buttoned them closed. She honestly looked much better in my jeans and v-neck t-shirt than I did. On the other hand, I don’t think I pulled off her ankle-length skirt and black top (with built in bra) quite as well as she did. The skirt was comfortable though. I should wear one more often.

Everyone left the room to go smoke except for Stef and I. She put the stopper in the door so that they could get back in to sleep and we both got ready for bed. I took off her clothes. She took off my clothes. It was not as cool as it sounds. Remember, we were wearing each other’s clothes. I made it to the bed and I was exhausted, absolutely wiped out. I nearly fell asleep before Stef came upstairs and laid there next to me. We talked for a bit, and beyond the overbearing need for sleep, the only other strong desire I had was to kiss her.

I can be fairly awkward when it comes to making moves on women. When I say fairly, I mean that this was probably the fifth time in the 2011 calendar year that I had been on, in or near a bed with a woman and had not been able to, or was hesitant to, go for a kiss. I have trouble knowing when the moment is right or reading whether it’s an impulse which will be reciprocated. Almost everyone tells me that if there is a woman on, in or near your bed, she probably wants to kiss you. I try not to assume so much. My past failings aside, I manned up (kind of) and asked Stef if I was allowed to kiss her. She obliged. We kissed for a little while but to no fault of Stef’s, I was struggling to stay awake. I was trying to psych myself up but it was not working. I laid my head down next to hers for a brief minute.

“Fuck.” I was sleeping.

Okay. I was awake again. It was the middle of the night, maybe morning, and Stef was asleep next to me. I got under the blankets and drew my body in against hers. She had been a stranger a day before but by then, I felt no discomfort in being the big spoon. It was a Christmas miracle.

—Sunday, July 10, 2011—

I woke in the morning, glued to Stef, and looked across the king sized bed, noting how little of it we were taking up. Both of us combined occupied just a slice. Just a sliver. I rolled over onto my back and returned to my dreams.

“Fuck.” I was snoring. I knew it.

I can actually wake up sometimes knowing that I’ve been snoring. It is not a good way to wake up the first time I share a bed with someone. It’s very embarrassing and something I am moderately insecure about.

The two of us eventually got up and noticed that no one had ever come back to the room. Instead, they piled like sardines into another, much smaller room. When we met up with them, they gave some excuse about not knowing where Stef’s room was located but there is a part of me that thinks they intentionally left Stef and I alone. Maybe that wasn’t not the case. Maybe it didn’t matter because nothing particularly crazy happened. But if that was their intention, those were good friends. Get it girl.

Things were gathered and people assembled. I said goodbye to everyone and especially thanked the bride and groom for sharing such an important part of their lives with me. It really did feel special. I felt like I had seen these people at their best, or at least as good as they can be when drinking for an entire day. I felt like I had ever so slightly extended my network of friends that weekend.

Stef walked me to my car and we thanked each other. We had a good hug and said our goodbyes. I got into my car and made tracks for NYC.

“Fuck yeah.” That was awesome.