Ferry Ride Date

–Sunday, June 17, 2012–

Gather round, ladies and gentlemen, for the dating sensation of the summer season!

IMG_2078In this edition of One Hundred Dates, our hero (that would be yours truly) takes to the waterways of New York City on a mission to impress a Bible Belt gal and dance to that big band jazz music.

First thing’s first, folks, let me tell ya how this dame Dorothy saved my rear end.

My intended date for the day, Jamie, contacted me the night before and told me she’d have to cancel. Well, horsefeathers, that was no good! It was only 30 minutes before I was set to meet my Bartender Date; I was on my way to Manhattan; and I’d already dropped some dough on tickets to the big dance. I had to come up with something in a jiffy and that was when I thought of Dorothy.

Dorothy and I had come across each other on OkCupid and, though we were a 98% match, I didn’t drop her a line. See, towards the end of the project, everything was so flying by so fast that I wasn’t properly taking care of my online dating persona. Plus, she wasn’t any old tomato, she was a real Sheba and I didn’t want to waste her time. It was a dream that a doll like her would choose me from the wealth of men available online. I mean, she had it.

I was a lucky duck though, because she reached out to me that Friday with the following message, which blew my socks off.


I’m [Dorothy]. I was going to try and be all coy and wait to see if you messaged me but I was too intrigued to wait and judging from your Tumblr, you are unbelievably busy so I thought I’d just message you. 

So I’m [Dorothy]. I’m also a writer who is fascinated by love, sex and dating. I’m not huge for online chatting so let’s have coffee. 

In any case, good luck with your show tonight! 



(I never give out my number on here- so this a special exception 😉

PS I happen to adore skinny white guys.



Thanks for the message and to hell with being coy – you assessed the situation perfectly! 

You seem really great and I love your sense of style – you’re super cute. I have also found that I like most everyone young woman I’ve met from Tennessee, so that’s exciting. 

And yeah, I have an improv show tonight but I am always more inclined to meet than chat online, so I’ll shoot you a text. it might be tough in the next few weeks, but we can fit something in. 

Nice to “meet” you! 


PS – Thank God for women like you because without them, us skinny dudes would be nowhere.

And how!

Honestly, I didn’t think I’d get a chance to take her out until the project was over, but I wanted to stay in touch because she was a real looker and we seemed to have a lot in common. We were already passing messages that day and, as I ran through potential women I could ask out at the last minute (Mostly women I’d already dated), I felt I had to try her. 

Normally, I wouldn’t have asked someone I’d so recently made contact with to do something last minute, particularly if I saw real potential in them. It didn’t make the best first impression. The women I’d previously dated had already given me a break and since I knew them, I would feel less bad asking for a favor. But I was in dire straits, so I texted her with a desperate plea.

Me: What are you doing tomorrow?

Me: Because my date just cancelled and I am wondering if you’d like to go to Governors Island.

Me: Sorry to be rude! X_x Just let me know. I’ve actually got to go on a date right now.

Dorothy: Sure I’ll go.

Hot dang! Now, this was a gal for me! I gave her a few more details but put my phone away to go on Bartender Date, half expecting that Dorothy would wake up in the morning and realize what a Dumb Dora she’d been.

The next morning was the true test. I texted Dorothy to see if she was willing and able to travel to Governors Island with me, and much to my pleasing, she wasn’t just teasing.

It was a leap of faith since I hadn’t told Dorothy much about The Jazz Age Lawn Party, which we would be attending that afternoon. A recent biannual tradition in New York City, the Lawn Party was a big old-fashioned gathering in the style of the prohibition era hosted by Michael Arenella and his Dreamland Orchestra. Cocktails and coattails abounded as folks dressed up and drank down in the spirit of the 1920s. I’d heard the 2011 edition had been ducky and was eager to see it for myself in 2012. Better yet, the only way to get there was by ferry, effectively knocking off one of my dates in fashion.

I told Dorothy I’d meet her by the covered subway entrance at Union Square and headed into Manhattan a little early. I had to stop by my office to pick up a spiffy new shirt that I’d bought the day before and had dropped off for safe keeping. After all, I wanted to look nice for the event and if a new white shirt was going to do the trick, then I had to have it.

Coming up from the subway stop, it was easy to spot Dorothy in her black and white polka dot dress, complete with a red floral headscarf. She was a real deb with her bright red lips, beautiful smile and elegant chassis, greeting me with a big, friendly, Southern hug. You never knew about people you met online, but she was the genuine article! That was why I always told people who hated online dating that they were full of baloney. The web had just as much potential for success as meeting someone at the gin mill.

Given the short notice of our interactions, I almost didn’t believe she was there and as keen as I’d hoped. I was also relieved to see that I wasn’t the only one on the date who had dressed up.

We didn’t waste much time standing there as we had our journey to Governors Island to chit chat and made our way down to the catch the 4 train. Riding the rails, we found other party goers en route, all dressed like they were from the same vague thirty-year time span. I say, it’s incredible how many different interpretations for “Jazz Age” you can come up with when digging through your closet.

Dorothy had only been in New York a very short time, having recently graduated from university in Tennessee. That’s right, she was young — 21 years young to be exact — but I was used to being a funny old daddy. It made me feel a bit uneasy, sure, but Dorothy didn’t come off as some kind of impressionable young mind that I would corrupt. I could tell quickly that she was more vamp than canceled stamp.

Plus, the nice thing about a younger woman was that they were rarely looking to middle-aisle.

She was a working gal at a PR firm with bosses she loved, but was underemployed at the time and searching for something more permanent and higher paying. (Ain’t we all, darling?)

Though she had been raised in Kentucky and schooled in Tennessee, Dorothy’s parents were living in California at the time. I was hoping I could relate a bit, as the son of a California native, but our families lived at opposite ends of the Golden State – which made them about as similar as whiskey and water.

Making our way to the ferry building, we ran into all kinds of folks in their glad rags with the same destination as us. Many of them were carrying picnic supplies, or at the very least, blankets and the like. I hadn’t thought of it as a picnic environment, but then again, it was a lawn party. I felt a bit like a sap, having not prepared thoroughly, but I seemed to get a pass from Dorothy since it was both our first time. We had no idea just how well equipped and enthusiastic many of the attendees would be.

The ride over was short, fun and made the date ab-so-lute-ly official. The ferry to Governors Island didn’t cost a single clam, and while it was not a Ritzy way to make the journey, it served its purpose just fine. We’d done it: we bought a zoo we rode a ferry. In no time, it was all over, but the view was great while it lasted.


Dorothy and I followed signs and the mass of young cutie pies to the lawn where the party was taking place. It was a sectioned off portion of Colonels Row and by the time we arrived, it was bustling with activity. There were ticket takers at the gate, tents set up around the perimeter selling goods, food stands dishing edibles and of course, at the far end of the lawn, Michael Arenella and his Dreamland Orchestra playing music to a lively dance floor.

I felt a bit uncomfortable handing over our tickets, as one of them had another woman’s name on it, but I think Dorothy understood that I’d been cancelled on, so she cut me some slack.

Once we were inside, I swear it was a dreamland – the orchestra had been aptly named. It looked classy and well put together without being so swanky that people like us would feel out of place.

Everyone walked around in their best attempts at 1920s garb and while there was an abundance of flapper dresses and bow ties, you could tell there were some real pros as well. There wasn’t a rag-a-muffin in the bunch. We visited some booths with old time clothing and discovered that Dorothy had quite the eye for fashion. I would have loved to own some proper rags from the time period, but it was an expensive hobby for things I would only wear on rare occasion.


We passed on the opportunity to have our photo taken sitting on a large, waning crescent moon, as we’d have to pay to see the actual product, but it was a fun feature. I was no piker, but it was certainly overpriced. We were more inclined to investigate the St. Germain (Official sponsor) bar set up on the other side of the lawn, anyway.

I asked the barkeep for a couple of cocktails (All of them were St. Germain centric) and he asked us for tickets. Well, buddy, we didn’t know nothing about no tickets! He told us that we had to buy food and drink tickets if we wanted to purchase anything from the corresponding vendors, but since we hadn’t known that, he told us the first two drinks were on the house. Now, that was just the bee’s knees! And I’d never had a St. Germain cocktail before, but if you liked things sweet and refreshing, as I did, it was the berries.

Cocktails in hand, Dorothy and I were free to ankle around the grounds a bit and we spotted just about the cutest little kid ever, dressed up as a sailor. Dorothy maintained that she had dressed once as an even cuter sailor when she was a young babe and that there was a picture of it out there somewhere. I’m sure she had been adorable. After all, everyone looked better in uniform. Lucky for me, we didn’t see many grown up bell bottoms or fly boys that day, or else I would have looked like a real plain Joe.

IMG_2082Over on the dance floor, we watched some of the hoofers cut it up for a little while and – let me tell ya – there were some serious Oliver Twists in the bunch! I didn’t have the confidence to ask Dorothy to dance though. While I was okay on a dance floor by myself, I didn’t know the first thing about couples jazz dancing. You’d think, having recently gone on a Dance Class Date, that I’d have had a little more confidence, but this was a different ballgame. I’d need to have a bit of an edge before I was ready to drag her out to the floor.

Arenella, the apparent big cheese of the operation, had his band take a break and left the phonograph to entertain the sea of dapper young folks. Dorothy and I took the opportunity to wander the lawn some more and to get to know each other. In our talks, we discussed music quite a bit. She seemed to be a gal who made it out to a lot of shows and even had friends in bands. Typical – an attractive young lady from Tennessee with her pulse on the music world.

We got ourselves some more giggle water from the St. Germain outpost, but this time we made sure to buy drink tickets in advance. We also made sure to pick up some food tickets for later.

As we walked through the patchwork of picnic blankets, chattering friends and adorably dressed lovers, Dorothy stopped me rather suddenly. She had spotted a male fashion blogger that she recognized. He went by the name of This Fellow and she knew him more so because of his fashionista girlfriend, Keiko Lynn, who Dorothy searched for, but couldn’t find amongst the crowd. [Fortunately, Keiko had been there and you can see what the party looked like from her point of view on her website.] I was impressed that Dorothy recognized a man in passing simply for being a pretty boy on the internet, but then I learned about her pretty little secret.

IMG_2084Dorothy had mentioned, in her original message to me, that she was a writer herself. Well, it turned out that Dorothy was a beauty and fashion blogger, but more than that, she was a beauty and fashion vlogger. On her own website and YouTube channel, she made videos which ran the gamut from make up tutorials to outfit reviews to interviews with other stylish ladies. While she wasn’t making her living from her internet presence yet, she was gaining popularity and experience.

It was crazy to find out, a bit later, that she had thousands of followers and regularly received complementary products from various brands looking to use her website to gain exposure. She even maintained a parallel YouTube channel in French, because guess what, she was fluent! I had completely sold myself on the idea that Dorothy was a hip dressing, music scene hanging, recent college graduate simply trying to figure out life in New York when in fact, she was the star of her very own fashion and beauty channel and had been at it for some time. I suppose that didn’t negate the other things I’d thought about her, but I had certainly underestimated her. She really knew her onions when it came to looking swell.

I had the curiosity of a hundred alley cats to get home that night and look her up online.

IMG_2083Since she was used to getting all dolled up and putting her looks on display, I finally asked her to level with me: Which celebrity did she look like? Ya see, in her online profile, she’d mentioned that she was often told she looked like a certain celebrity and I thought right away that I knew who it was, but that movie star wasn’t in the best of shape at the time, so I thought it might offend her to make my guess. Being playful, she asked me who I thought she looked like. What a tricky little turn. I had to come out and say it: She looked a whole lot like Lindsay Lohan, in her best years, of course.

Well, I was right. Although the comparison with Lohan was somewhat less than favorable at that time, she’d been a sexy Hollywood up and comer not too long ago and the similarity had everything to do with them both looking their best. As such, Dorothy didn’t shy away from her obvious doppelgänger.

It was no surprise when a photographer stopped us a bit later to ask Dorothy for a photo. I stepped aside and allowed the true belle of the ball to have her portrait taken.

Dorothy and I wandered back towards the dance floor and after spending some time watching, and finishing our cocktails, we decided to take the plunge. There were plenty of other couples out there who didn’t know a Fox-Trot from a Charleston, so it felt safe enough to attempt.IMG_2081

Although we probably looked like we belonged at a common rub, there were no fire extinguishers to be found and, most importantly, neither of us was better than the other. We were able to stumble through our first extended physical contact without feeling too bad or awkward about it. Playing it safe with the dance steps and watching where my hands went definitely helped. After all, I didn’t want to take any wooden nickels.

After our foray into couples dancing, we needed to simmer down, so I suggested a stroll beyond the lawn to explore the grounds of Governors Island. The weather was perfect for an afternoon walk and we completed a nice big loop while talking about all manner of things. I was able to ask about fashion and all of that after I found out about her hobby, or rather, career in the making. I’d been much more interested in fashion lately and we talked about how it was used as a form of expression.

I was getting to know Dorothy better and better and I liked everything I heard. She was laid back and hip all while being flirty enough to keep me on the edge of my seat. Being out with someone so easy to talk to was a blessing, especially someone like Dorothy, who would razz me a little bit too. I loved that playful nature. Also, I was impressed that she was willing to go for a long walk in her heels. Her dogs must have been barking by the end of it, but she didn’t beef once.

When we returned to the dreamland of the jazz age, we concurred that it was time for a bite to eat. We went to the food stands and picked up sandwiches and beers. We found a little patch of grass that hadn’t been completely trampled yet and sat down to enjoy our food. The food itself was so-so, but as we sat there during the meal, I realized how much ground Dorothy and I had covered that day already. I’m sure it helped that we were two flirtatious individuals, but we’d become real comfortable around each other by lunchtime.

We continued to sit and talk after our grub was gone. There didn’t appear to be any desire to move on yet. We were resting after our walk and enjoying some relaxed time together. We were sitting close. We were being playful. We were looking at each other. We were…kissing.

Now you’re on the trolley, Evander!

I mean, sure, it didn’t just happen my chance. I could tell Dorothy was reciprocating my flirtation and advances, but I didn’t know if today was going to be a cash or check kind of date. All friendliness aside, the bank coulda been closed – it was Sunday after all – and I coulda ended up the recipient of an icy mitt. 

Some women were so darn friendly with every fellow they met — and she’d done me a real solid by even going with me that day — that I didn’t want to jinx nothing. I was right in making my move though, as I found Dorothy more than reciprocating. She turned out to be quite the little bearcat. We were kissing up such a storm, I had to take my cheaters off!

We stayed there, enjoying the sparks that were flying and before we knew it, we were necking. The lawn wasn’t a petting pantry though, so before it got too heavy, we snapped out of it. Dorothy, all proud like, informed me that I was wearing some of her red lipstick. I laughed and wiped it off with a leftover napkin from lunch.

Having reached the milestones of both lunch and kissing, we went back to the dance floor to give it another go. We never figured out any of the precise dance moves of the experienced hoofers surrounding us, but we looked better than our first time out and with a few kisses thrown into the mix, it was a grand old time.IMG_2079

The party was winding down and it seemed like fine time to blouse. Dorothy and I walked back the way we’d come, towards the ferry, but stopped along the way. We bought some lemonade from a cart and stood on the northern edge of the island, looking at lower Manhattan as the sun reflected off of the glass towers. It was absolutely beautiful. And though the day was still quite pleasant, the winds whipping up around the island were a bit chilly, so I gave my blazer to Dorothy and hugged her. We’d talked a lot that day so rather than beat our gums, we stared out at the skyline, kissed a bit along the way and finished our lemonade, soaking in each moment.

As we approached the ferry docks, we could see that the lines were incredibly long. Just then, someone mentioned that there was also a Brooklyn ferry a little further down the road. On we walked and rather soon, we found another ferry landing with two lines. The man in charge said that the ferry with the big line, and inexact departure time, would be free, but if we wanted to shell out a few rubes, we could be on the next ferry out of there and jump in the shorter line. I paid the piper and we waited in line for about 20 minutes for the next ferry to arrive. It was a nifty maneuver to get off the island in a jiffy.

The ferry ride was the most frigid part of the day, but Dorothy had my blazer and my arm was around her all the way to Williamsburg. It was swell having her on my arm, because I ain’t no bimbo – it was getting cold out there and the body heat was welcomed.

That whole ride was quite copacetic. Dorothy nestled into my body and hugged me the way your best girl would. It was already a picturesque ride up the East River and to have such a lovely woman sharing it with me in a manner such as that, it was deeply satisfying. She must have been freezing her gams off, but she made it to Brooklyn.

There was no reason for our date to end and dusk was just settling in, so we decided to find a juice joint to have a drink or two. I thought of Beco, which wouldn’t be a far walk home for her and I’d been there once before, in my pre-OHD days. It was a Brasilian place so the cocktails had some extra flavor to them. We sat at a two-top, gabbed until well after the sun had fallen out of the sky and found that one round of hooch would be enough. It was Sunday after all, no time to get ossified, so we decided to get a wiggle on. Plus, I was happy to save some jack after a day of paying for everything.

I was on a gentlemanly streak with the whole blazer thing, so I figured I should walk her home as well. Also, I’d be lying if I said I wasn’t hoping to see the inside of her place. When we reached her building, we stood outside kissing, then necking and got all the way to some heavy petting. 

Despite the theatrics, I wasn’t invited up. Ah, applesauce!

She knew how to keep me wanting more and as I turned and left, I knew I was enamored. Sure, I wasn’t goofy just yet, but I was carrying a torch for her. Dorothy knew how to play the game and she wasn’t no flat tire. I could only hope she thought I’d hit on all sixes too.

Twenty-four hours prior, I had been in a real tight bind, willing to go on that date with just about any Jane, and I sure did luck out with Dorothy. Between the project ending, meeting this amazing gal and having other dames I was interested in, I could see myself getting real balled up real soon. After all, I was a total pushover, historically.

For the time being though — as I rode the train back to Queens — everything was Jake.