Posts Categorized: Person Based

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 »

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 »

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 »

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 »

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 »

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 »

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 »

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 »

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 »

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 »

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 »

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 »

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 »

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 »

Random Person Date

—Saturday, November 5, 2011— Sometimes you just have to take a chance, even if it seems like it’s from out of nowhere. It was roughly 2 a.m. on a Thursday in August of that year when I sat down on a grungy wooden bench at the 49th Street N/R/Q stop and looked to my left…. 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 »

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 »