Posts Categorized: Any Season

Mom Date

—Tuesday, June 26, 2012— If you’re having girl problems I feel bad for you son, I got 99 problems but a mom ain’t one. In fact, this mom was the opposite of a problem — she was my 100th date! For all the preparation I’d done throughout the year, it was actually kind of unnerving… Read more »

Art Gallery Date

—Tuesday, June 19, 2012— It was easy for people to dismiss OHD as not being genuine, or real, for one reason or another, but really, it was all subjective. The same had been said about pieces of art, time and time again, by countless college freshmen. Not matter how you sliced it, art and dating… Read more »

Bartender Date

—Saturday, June 16, 2012 — One myth I wasn’t able to truly able to debunk during OHD? That female bartenders were the most impossible dates to get. I found a way to make it happen, of course, but it wasn’t easy. A week before this date, I had come home after a long Friday at work and… Read more »

Dance Class Date

—Tuesday, June 5, 2012— Dancing was something I really enjoyed doing, but the idea of a classroom setting tripped me up. I was nervous to go from being a decent dancer in my demographic to doing things incorrectly in a class. However, I was more nervous about my date not showing up. Admittedly, I was… Read more »

Foreigner Date

—Saturday, June 2, 2012— Foreign women — whoa baby. There were a number of female qualities that could draw me in and make me weak in the knees, but being from another country was probably A-number-1. I had been steadily reaching out to foreign women throughout the project, but none of those interactions had borne… Read more »

Co-Worker Date

—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… Read more »

LARP Date

—Saturday, May 26, 2012— A few dates made the list because they perfectly combined weirdness and curiosity. I had never LARPed before, but I knew that I wanted to try it at some point. I also knew that it would be a very unique date, at least for anyone who wasn’t already a part of… Read more »

Married Woman Date

—Saturday, May 19, 2012— Don’t be so closed-minded — married people needed to go on dates too. We all know that in 2012 the sanctity of traditional marriage was being destroyed by liberal hippies and their gay friends, so it wasn’t all that hard to find a married woman to go out with me. But… Read more »

Performance Art Date

—Friday, May 18, 2012— As soon as we first went out, on Bowling Date, I knew that I needed to go out with Pearl again. I was upset, however, that I had let so much time pass before asking her again. In the whirlwind of my OHD year, Fall had turned to Winter and Winter… Read more »

Sister Date

—Friday, May 11, 2012— Sister Date was one date that people often had questions about. Wasn’t that incestuous? Totally gross?? Morally incomprehensible??? Well you can calm down…because I don’t even have a sister. I had to date someone else’s sister for this one. The original idea was that I had to go out with the… Read more »

Community Service Date

—Saturday, May 5, 2012— In most ways anyone could view it, this OHD project was all about me. I was the one benefitting, getting the credit, putting forth opinions and, hopefully, growing as a person. It seemed to make sense that I should at least have one date where the goal was to give back…. Read more »

Notable Individual Giving A Talk Date

—Thursday, May 3, 2012— I couldn’t believe that for a date activity as mundane as a notable individual giving a talk, I had found such a seemingly exciting woman who was willing to tag along. Unfortunately, this date didn’t go according to plan and I nearly had to call the whole thing off. Radha had… Read more »

Craigslist Date

—Thursday, April 26, 2012— Craigslist: The Wild West of internet dating. There were no real rules on Craigslist, a site where people placed ads seeking and offering any and all kinds of intimate encounters, even prostitution was offered up there. By 2012, was a taboo place to seek out a date and that was exactly why… Read more »

Breakfast Date

—Friday, April 20, 2012— Even the best laid plans could go wrong. But this plan was pretty cool. It was adventurous even, especially considering that it revolved around a meal that many people simply skipped. Isabelle had emailed me almost a month before our date, after she had stumbled upon my tumblr via her tumblr, or something… Read more »

Ex-Girlfriend Date

—Friday, April 13, 2012— It had been just over nine months since Alana and I had seen each other. Nine months since I stood on her stoop, returning a book I’d borrowed. Nine months since I’d apologized over and over again for having to start this project and for having to break things off with… Read more »

Video Chat Date

—Thursday, April 12, 2012— For as long as I could romantically recall, I’d always wanted what I couldn’t have and, given that she lived all the way across the United States, Jen Friel was no exception to this rule. However, it did make her a great candidate for a video chat date. I wondered if wanting… Read more »

Celebrity Date

—Sunday, April 1, 2012— Finding a celebrity to date was certainly a tall order to fulfill, even with a year to do so and my amazingly good looks. Fortunately, a friend hooked me up with a celebrity date who was even better looking than me and incredibly down to earth. Crazy, I know. Then again,… Read more »

Suburbs Date

—Friday, March 30, 2012— Admittedly, this date was supposed to be with someone else. In fact, it was supposed to be spent with the only person from my high school I’d ever considered an enemy, which would have been perfect for a date in my hometown, but alas, that fell through. Maybe another time. Maybe… Read more »

Midwestern Date

—Tuesday, March 20, 2012— I didn’t have a specific plan for how this date would go, as it merely required the presence of someone from the Midwest, and fortunately, I wasn’t given too much of a chance to over-think it. This date started off as a different date and while I had made plenty of adjustments… Read more »

Scavenger Hunt Date

—Sunday, March 18, 2012— I love a good scavenger hunt. They’re filled with surprises, you have to piece together clues and at the end of it, you usually hope to win a prize. I love the competitive aspect of it too. This scavenger hunt was unlike any I had ever been on because the prize… Read more »

Club Date

—Friday, March 16, 2012— You know what I always say: Don’t be a schlub in the club. This date was definitely the one time I had to worry about that the most, since I’d actually be in a club for once. Hopefully, I wouldn’t be a schlub. This date all began on OkCupid with some… Read more »

College Friend Date

—Friday, March 9, 2012— I hadn’t seen Billie since the winter of 2007 and I missed her more than I probably realized, burning through my days in NYC while she went about her own life in sunny LA. All it took to close that nearly 3,000 mile gap was several hundred dollars, a vacation day… Read more »

Double Date

—Tuesday, March 6, 2012— Double your pleasure, double your fun, right? The logic seemed sound enough. When Morgan and I had gone first gone out, back in October of 2011, we talked about our friends Bradley and Georgia. They seemed like they might be a decent fit for each other, but it took me forever… Read more »

Unplanned Date

—Saturday, March 3, 2012— It was about 10:20 p.m. on a Saturday night and I was sitting in my apartment, taking notes that afternoon’s Lunch Date, and I had just watched a two hour episode of Downton Abbey. It was only then that I saw that I had a message in my OkCupid from a woman… Read more »

Lunch Date

—Saturday, March 3, 2012— For one reason or another, lunch dates seemed to be relegated to the province of weekday office breaks and spur of the moment decisions to eat together. On the weekends, brunch reigned supreme and lunch seemed to take a couple days off. When I asked Sandra to lunch, for our second… Read more »

Gay Date

—Wednesday, February 29, 2012— Throughout the first seven months of One Hundred Dates, I had spoken to various friends and random gay men about how I should go about getting this date. People had various opinions and gave sometimes contradicting advice, but luckily for me, my Gay Date fell right into my lap. One of… Read more »

Laundry Date

—Tuesday, February 21, 2012— By nature, I was a procrastinator, and while laundry was something that I definitely tended to put off, eight months was a really long time. To be fair, I had “done laundry” in the previous eight months. However, this was the first time I’d actually washed my own clothes since moving… Read more »

Older Woman Date

—Tuesday, February 14, 2012— I had long wondered how Valentine’s Day would play out during OHD, and while I hadn’t expected to be going out with someone 19 years my senior, it also didn’t seem like the craziest idea in the world, given what my world had become. Lois was ahead of me getting to… Read more »

Create A Podcast Date

—Sunday, February 12, 2012— Through parts of this day would come to exist on the internet, in audio form, it was actually one of the few dates that began in my home neighborhood of Astoria, Queens. Maybe it wasn’t actually so few, but it felt that way for whatever reason. One cool thing about my… Read more »

Dim Sum Date

—Saturday, February 11, 2012— Good advice for just about any first date? Try something new. Or at the very least, give your date something new to try. Such was the case when Paige and I traveled out to Flushing, Queens for dim sum. Paige and I met up at noon on the top level Queensboro… Read more »

Shopping Date

—Sunday, February 5, 2012— It was Super Bowl Sunday and the New England Patriots, my hometown football team, were playing against the much hated New York Giants. Rather than watch the game, I was going out shopping, because One Hundred Dates had a wonderful way of ruining my life. My date for the day was… Read more »

Exercise Date

—Tuesday, January 31, 2012— Lara’s approach was not what I had expected. She walked up to me so casually, I had no idea she was my date, and yes, I had seen a picture of her before. “Hey, I’m Lara,” she said with no inflection or emotion behind it. “Lot’s of people hug, but that’s… Read more »

Spend No Money Date

—Sunday, January 29, 2012— While riding the 2 train into Brooklyn, I watched two teens debate how to properly ask someone on a date. One young woman was adamantly telling a young man not to ask, “Want to hang out?” She told him he had to ask a woman on a real date. It had… Read more »

Nothing But Shots Date

—Friday, January 27, 2012— Valerie was supposed to go out with me months before this date and by that I mean, I was supposed to ask her out months earlier but I never did. I was also supposed to ask her on this date because she worked for a vodka company, so it seemed like… Read more »

Off-Broadway Date

—Saturday, January 21, 2012— It had been a long week and I needed a pick me up in more ways than one. Originally, I was supposed to take someone else on this date, but when that fell through, Dora got the call. I was three weeks into the second half of the project and it… Read more »

Afternoon Tea Date

—Monday, January 16, 2012— I always appreciated a long weekend, and throughout One Hundred Dates, having a Monday off from work was even better than usual. It meant I could get some sleep, catch up on writing or go on a date. I did all three of those things on Martin Luther King Jr Day… Read more »

Blind Date

—Friday, January 13, 2012— It was Friday the 13th, and I was in a real bonerjam. Two out of my last three dates had cancelled on me, which meant I was two dates behind pace. I was about to wrap up the first two weeks of 2012 with only one date under my belt. I… Read more »

Brewery / Beer Tasting Date

—Sunday, January 8, 2012— It was my brother’s birthday, but I wasn’t home in Massachusetts for it. Rather, I was embarking upon my first date of 2012, heading to Brooklyn Brewery in Williamsburg with a woman from the internet. She found me on OkCupid, was enthused about the project, and suggested the brewery since it… Read more »

High School Friend Date

—Saturday, December 31, 2011— Wow. I am still somewhat surprised. My 50th date of the project hit at exactly the six month mark. I was incredibly relieved that all the hustle I’d put in had gotten me right where I needed to be. Sure, I may have only been half-way there, but it encouraging to… Read more »

West Coast Date

—Tuesday, December 27, 2011— “I wish they all could be California girls.” — Words of wisdom from David Lee Roth Christmas had come and gone over the previous weekend and I had shuffled down from the Napa Valley back to San Francisco. It had been a great trip thus far — went on a wondering… Read more »

Man Date

—Wednesday, December 14, 2011— Madison Square Garden — One of the greatest stages on Earth. My Morning Jacket — One of my favorite bands in the world. Me — Eating pizza alone and wondering when exactly I would see my date for that night. I started my date that night on my own because David… Read more »

Cooking Dinner Date

—Saturday, December 10, 2011— I met Emma inside of the 23rd Street entrance to New York City’s own amusement park of Italian food and drink, Eataly. I hadn’t seen her since January, at the same party I had met Soul Mate, almost a year earlier. She caught me by by surprise, arriving from the interior… Read more »

Hookah Bar Date

—Wednesday, December 7, 2011— We had agreed to meet at the restaurant, Le Souk Harem, which I had read mixed things about online, but upon arrival, it seemed decently cool. Since I was a bit early, I grabbed a seat at the diminutive downstairs bar. The bartender, a young guy who couldn’t have been older… Read more »

Acupuncture Date

—Saturday, December 3, 2011— First dates put many people a little on edge. Most aren’t sure how to act, don’t know what is appropriate, and yet they want everything to go perfectly. Whether it’s nerves or excitement, most of us are waiting on pins and needles each time we set up a date. It was… Read more »

Moustache Date

—Friday, December 2, 2011— I present to you, ladies and gentlemen of the internet, a moustashioed date in two parts. We begin with the prologue. A friend of mine from college, Jenna, texted two weeks before this date, in late November. When Jamie texted me the Sunday before our eventual date, asking if I’d like… Read more »

Movie At Home Date

—Sunday, November 27th, 2011— A second date with a fellow dating blogger sounded like fun and a movie at home on a late November Sunday felt like the perfect choice.   As with the first time Ally and I went out, I arrived at the her subway stop in Greenpoint, Brooklyn early. This time I… Read more »

Build Something Date

—Friday, November 25, 2011— A date, like many things, is best created piece by piece, assembled by hand and created as a team. Both people need to be on the same page in order to build something that will last. I was headed to Mikaela’s apartment for our second date. It was my second second… Read more »

Meet the Parents Date

—Thursday, November 24, 2011— My head was killing me by the time I arrived at Penn Station for my 11 a.m. train. I was out the night before with Betsy, my Broadway Date, but I didn’t drink very much and it hadn’t been a late night, so I didn’t know what was causing the terrible… Read more »

Work Function Date

—Saturday, November 19, 2011— I was in Boston this weekend for my company’s holiday party, and on Friday night, I had gone out with Julie. It was the second time I’d seen her since she’d been my date to Comic Con a month earlier. Both such occurrences had been “off the books”. This would have… Read more »

Board Game Date

—Monday, November 14, 2011— Aside from man himself, there is perhaps no game more dangerous than the dating game. It eats some of us alive, spits us out and carries on to the next unsuspecting victim. I don’t like to think of it as a game, but there’s no denying that even the language of… Read more »

Travel Date

—Friday, November 11, 2011— Walking to Penn Station, I stopped to get some snacks for the train ride. I felt somewhat unprepared for travel without snacks — they were essential to passing time. Plus, I couldn’t forget to bring some water — the lifeblood of a good date. The air was a bit cold in… Read more »

Art Class Date

—Thursday, November 3, 2011— Art is subjective. As is dating. I was asked often over the course of the project, “What is a good date?” and much like good art, it is often left up to the audience to decide. I was meeting Selina just south of Madison Square Park, on Broadway, in lovely New… Read more »

Shooting Range Date

—Saturday, October 29, 2011— ZOMBIES! It was the Saturday of Halloween weekend and I couldn’t think of a better way to celebrate than by taking a zombie apocalypse handgun training course. I mean, right? Since I had been up late the night prior, at The Rocky Horror Picture Show, and I’d had an illness-ridden, busy… Read more »

Rocky Horror Date

—Friday, October 28, 2011— I’ve hardly ever been cool enough to be well versed in cult classics. I’ve always thought that the people knew every great B movie, every criminally underrated band or every avant guard comedian were somehow ahead of the curve and had a bold predisposition to exploration which I lacked. The Rocky… Read more »

Bowling Date

—Sunday, October 23, 2011— This was the cherry on top of what had been a crazy ass weekend. My bus from Boston had pulled into town only a couple hours before the date. I ran home to Queens with just enough time to change clothes before turning right back around and returning to Manhattan. That… Read more »

Cocktail Date

—Friday, October 21, 2011— It had been almost eight months since I’d been in Boston, since I’d been back in my home city, and it had been even longer since I’d been in love. Sometimes you just know when you’ve been away too long. I was two beers deep and feeling sleep deprived after taking… Read more »

Comic Con Date

—Saturday, October 15, 2011— Here’s what I love about my favorite comic books: They allow me to engage with something fantastic while still making me feel like they are possible in real life. If only I were bitten by the right spider; if only they would invent a flying suit of armor; if only an… Read more »

Broadway Date

—Thursday, October 13, 2011— It should have been a super fun and carefree Thursday. Here was my agenda: 1. Sleep in. 2. Do some shopping. 3. Go to work. 4. Attend a Broadway premier. 5. Attend the after party of a Broadway premier. This night was Broadway Date, and it wasn’t just any show, it… Read more »

Write & Record A Song Date

—Saturday, October 8, 2011— I spent most of the morning cleaning my apartment because Cara would be spending a good chunk of time there that day and I wanted it to look like I was both sane and somewhat orderly. I also needed to set up and test my recording equipment, which I hadn’t touched… Read more »

Trivia Date

—Tuesday, October 4, 2011— I really needed a date for the night and I was running out of time. I had been wanting to take Megan out for a few months and luckily, I had just run into her that past Saturday, so it wasn’t totally out of the blue to contact her about a… Read more »

Dive Bar Date

—Saturday, October 1, 2011— It was about a quarter past ten at night and I am certain it was the latest I’d started a date so far. I had left my friends at a bar in Chelsea and headed down to the West Village. It only took me a few minutes to get my bearings… Read more »

Live Music Date

—Sunday, September 25, 2011— “You are the only thing in any room you’re ever in.” – Elbow, Starlings I was supposed to meet Lynn around 5:30 or 6 p.m. in Hell’s Kitchen. There was a Thai place there that I liked. She texted me around 4:15 p.m. from the PATH station in Hoboken, letting me… Read more »

Tattoo Date

–Saturday, September 24, 2011– Why was I waking up at 7 a.m.? I was way too tired to be up so early. After a week of jet lag following a trip back from Hong Kong and having to pull an all nighter for work that Tuesday, I was absolutely exhausted. I didn’t need to be… Read more »

A Broad Abroad Date

—Monday, September 12, 2011— I had studied abroad before. I had even studied broads before. But never had I ever studied broads abroad and my 2011 trip to Tokyo, Japan was a one week crash course. I’d spent the better part of ten days observing the women of Japan and looking for some way to… Read more »

Spa Date

—Wednesday, August 31, 2011— This date just didn’t want to happen. Little Miss Havana and I were becoming star-crossed lovers. We were originally supposed to go to Governors Island two weekends earlier, but as I approached her apartment that day, dressed for a 1920’s dance party, the clouds over Manhattan and the forecast of rain… Read more »

Burlesque Date

—Thursday, August 25, 2011— Burlesque conjured up a number of images in my mind if I sat back for a moment and really thought about the word. I didn’t have a particularly good understanding of it, but I believed it to be part strip show, part side show and part comedic theater. For sure though,… Read more »

Open Mic Date

—Tuesday, August 23, 2011— I was going to need to overcome a couple hurdles that night. The first was one I was getting used to — attempt to impress a date whom I did not know. The second was far less familiar to me — I’d have to perform two songs I’d written at an… Read more »

Southern Date

—Wednesday, August 17, 2011— I expected the night to involve nothing more than a nice and pleasant date, which I was happy for since it was the third woman that I’d gone out with in as many weeks who did not know about the project. I was looking forward to her being the last. It… Read more »

College Girl Date

—Tuesday, August 16, 2011— The day in question was my first vacation day of 2011 and I took it in the name of One Hundred Dates. It felt fantastic to sleep in a little, run a couple errands, get some work done and then finally head out to start my day. Having plenty of time… Read more »

Silent Date

—Wednesday, August 10, 2011— Yes, of course I was nervous. Are you kidding me? Not only was I going on a very awkward, non-verbal date, but I didn’t even know the 36 year old woman who would be accompanying me beyond her How About We… profile. Furthermore, she wasn’t aware of One Hundred Dates, and… Read more »

Museum Date

—Sunday, August 7, 2011— The old rumor is that the average adult male thinks about sex every seven seconds. If that was considered high volume then this date was a record day, because sex was pretty much the only thing on my mind. Sex. Sex. Sex. Sex. Sex. Sex. Sex. My date, Lora, and I… Read more »

Brunch Date

—Saturday, August 6, 2011— Brunch: The adorable, always fun to have around, and just plain well loved member of the Meals family. Wholesome in its timing, but fun in its inclusion of alcohol. Always laid back and fashionably late, Brunch is definitely a fan favorite. Nothing messes with Brunch and it doesn’t bother to cause… Read more »

Comedy Date

—Wednesday, August 3, 2011— I was there pretty early. I guess I was about an hour early. That’s what happens when you don’t plan anything to do between work and your date. You end up staring at a mannequin in a wash tub while you have your first beer of the night. But then again,… Read more »

Truth or Dare Date

—Friday, July 29, 2011— Truth: I hate it when women see my apartment looking like a mess. For a few hours, I’d been cleaning my apartment and making sure everything looked decent while Norah rode the bus from Boston. I folded laundry, made my bed, organized the clutter, scrubbed the bathroom and assured that the… Read more »

Speed Date

—Wednesday, July 27, 2011— Once you get me going, I tend to be long winded. I like to talk, but for that to come out, I usually need to be in my comfort zone. Otherwise, I’m actually a little bit shy. I’ve never been one of those salesman or politician types who can bullshit with… Read more »

Secret Date

—Friday, July 22, 2011— Operation: SECRET DATE Location: CLASSIFIED Objective 1: Secure actual date with target Objective 2: Carry out date in secrecy Objective 3: Inform target of secret date Objective 4: Escape with life The target was contacted exactly nine days earlier. I was looking to see if Leigh would be in town that… Read more »

Fancy Dinner Date

—Saturday, July 16, 2011— Mia and I had been planning our date for over a month. When I finally nailed down the list of dates, I knew immediately that I wanted Mia to be my Fancy Dinner Date. She was a total foodie and even maintained a dining blog, so she was the obvious choice… Read more »

Movie Theater Date

—Friday, July 15, 2011— The employees of the 30th floor office at number 1633, Broadway, were proud to say that they were perfectly normal, thank you very much. They were the last people you’d expect to be involved in anything strange or mysterious, because they just didn’t hold with such nonsense. What then, was going… Read more »

Wedding Date

—Saturday, July 9, 2011— “Fuck.” 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… Read more »