The Experiment

Charlie is a lawyer turned entrepreneur who is usually either single or in a relationship–but rarely in between. Last fall, upon arriving in New York City, she challenged herself to 60 dates over a period of 50 days.

Phileas is a postdoctoral researcher who has had a few short relationships. Last summer, upon becoming newly single, he committed himself to 80 dates over 80 days in Boston.

Unbeknownst to them, they weren’t alone in conducting their respective experiments. When a chance connection came up, they shared experiences of ranking lists, awkward lip-on-lips and the story of a worn jean spot. The following exchange highlights a few lessons learned.

Why We Did it

Charlie: I started this because I was curious about online dating and the dating culture in New York. I had actually never dated before—I had always been single or in a relationship. So I made a spontaneous decision to sign up to something new!

Phileas: I was getting back into dating in Boston, but was having negative experiences. Some women were flaky, others just stood me up. I thought that if I increased the frequency of my dates, it might alleviate some of the negativity. Also, I love a challenge.

I initially planned to do 60 dates in 60 days, but got into it and extended it to 80 in 80 days.

Online, Speed Dating or In-person?

Charlie: I took it up as a challenge as well. Not all of my dates were from online, but the vast majority were from four different dating sites.

I went on a date every day throughout the fall, often with two to three dates crammed into a Saturday or Sunday.

Phileas: I only used two dating websites but also did speed dating and met in person. It took 3 hours per actual date with online dating and only 2 hours with speed dating. And the winner was meeting people in person—only an hour per date.

Charlie: I had to sift through lots of incoming messages. Disappointed by the men that would message me, I ended up reaching out to men on the site. On average I had to go through at least 7-10 rounds of messages online, then get or give a phone number, then go through more rounds on text before the date would happen. With a few men, the process took over 3-4 weeks to get to date one!

Phileas: Was that because you wanted to feel comfortable with them, or just because they were lacking initiative?

Charlie: What I found was that if I responded with a quick “can we skip this bullshit and just meet for a coffee?” men didn’t like it.

I took the “safe route” of waiting for the man to initiate a meeting. I have to say that I also reacted poorly to men who asked to meet too quickly. Usually, this meant that they wanted to get laid.

Phileas: That’s interesting, because asking to meet “too quickly” is pretty much what I did. I wasn’t particularly interested in sex, but I did want to avoid getting bogged down in mailing back and forth. How did you keep track of them all?

Charlie: I often used code names for the men and talked to my friends about them. They started to feel like guinea pigs.

I didn’t lose track, but my friends wanted an Excel spreadsheet just so they could keep up with the stories! Did you often kiss the woman at the end of your first dates?

Phileas: Only a handful of times. Maybe 6 or 8 of the 80 first dates.

Charlie: 95% of the men I went out with tried to kiss me on the first date. I became an expert at evasion. But, sometimes, I wouldn’t turn my face fast enough and I’d get some lip on lip!

Out of my 60 dates, I went on second dates with 3 of the men. The rest I’d follow up with a rejection text saying I wasn’t interested in dating but wanted to be friends. I genuinely meant it when I said I wanted to be friends, but I remained friends with only 2. The rest didn’t react well. That was a great disappointment.

Handling Rejection

Charlie: Did you feel sad when you didn’t get positive responses? Did the rejection wear on you? I feel that men are rejected the majority of the time…

Phileas: Online rejections are the easiest to bear, especially if it’s done nicely or passively (i.e. not getting back at all).

Speed dating rejections are a bit harder because you know they met you and still chose not to check the box next to your name. But yeah, the more you get rejected, the less it stings. Though in-person rejections still sting the most.

Charlie: I don’t think I ever got an actual rejection note. If a man wasn’t interested, I wouldn’t get a message after the first date. Or, if I had initiated contact online, I wouldn’t get a reply.

Phileas: I think the fringe benefits of rejection are enormous, since a lot of our life is spent not aiming high enough because of our fear of rejection. Not just in dating, but all aspects of life.

Charlie: Actually, being on the side of constantly sending out rejection messages was hard. I felt guilty and sad.

I didn’t want to hurt or be hurt. I started to value people less. I noticed that I would rank men that I dated and start losing sight of finding a real connection.

Phileas: That’s the danger of high-volume dating, which is why things worked out better for me after the challenge was over.

The Best of Times

Charlie: My final date ended up being a man I actually liked quite a bit, but it didn’t work out in the end. He introduced me to the concept of the “ranking list.” The men would admit, sooner or later, that they were dating multiple women, and that we were number X on their ranking list.

Phileas: I think I actually got very lucky. I didn’t meet anyone during my 80 dates, but I decided to do another 20 dates before stopping indefinitely. And it just happened that the 100th ended up being awesome, and we’ve been together for 3 months now.

When I told my current girlfriend that I had gone through 99 dates just before I met her, she was pretty shocked.

The Worst of Times

Charlie: One man offered to send me a limo with champagne within the first message. Of course, I said yes. I’m kidding. I blocked him right away and ran for the hills.

Phileas: One woman told me outright: “Hi, sorry to shut you down but I don’t like white dudes.”

I also had one date where I ended up talking for a total of 5 minutes during the course of 2 hours.

Charlie: I went on a date that I knew would be a complete disaster out of morbid curiosity.

The guy faked his college degree and asked if I would do anal in our first conversation.

He didn’t look like his photographs, was obnoxious and arrogant, and worst of all, rude to the waiters. He also called children “vomitous creatures.” I was itching to leave but didn’t want to be rude. We split the check. My friends said I was way too nice.

Phileas: The most awful date was one that came out of speed dating. We were having a not-too-bad conversation at a scenic spot. I had decided to make the best of it even though I wasn’t that attracted to her.

As I was sitting down I noticed I had a worn spot on my jeans and ran a finger through it absent-mindedly. Soon after, she made up some excuse to leave.

Later that night she sent me an email in which she accused me of…masturbating in front of her.

I hadn’t even touched the relevant body part (though I guess I should be flattered because the worn-out spot was way below the crotch)!

Lies, Misunderstandings, and Clarity

Charlie: I realized two things about myself from all those first dates. First, I didn’t have the heart to cut them short when I knew they weren’t going well (I would know within 2-5 minutes). Second, even if I wasn’t enjoying myself, the men would get the impression that I was. Probably because I tend to be bubbly and quite talkative.

Phileas: One thing I found was that misinterpretation and misunderstanding are rampant in dating, and that’s why I tried really hard to communicate clearly.

Charlie: I also found a huge discrepancy between profile and person. Especially when it came to what they looked like. And claims of having a sense of humor.

Phileas: For me it was the photographs as well. They were frequently taken from flattering/ deceiving/ special angles. A number had been photoshopped and re-touched.

Charlie: A good number of men lied about height. I found that anything under 5’10” would be inaccurate by 2-3 inches.

I also immediately ruled out any man who took a photograph of himself in a bathroom lifting his shirt. Or shirtless in any situation.

Phileas: A lot of the women I went out with didn’t offer to pay their share even though it was clear in both of our minds that we weren’t going to see each other again.

I’m still recovering from this financially, 6 months later! How do you feel about paying?

Charlie: I always offered to pay and meant it. Very few took me up on it though.

Reassessing Our Dating Criteria

Phileas: What were your criteria for seeking out men? And have they changed since?

Charlie: Physical attraction. Education level. Profession. Hobbies. Interests. Not sounding boring on their profile. Not sounding douchey. Humor was always a must. Also, just plain chemistry. I don’t think my base criteria has changed.

Phileas: For me education is still critical, as is intelligence and attractiveness, but I eased up on other things which were secondary (e.g. height or religion).

Charlie: Pre-online dating, I never really had very strict criteria. I found it odd to check off those boxes, but now, I find it easier to narrow down what I’m looking for.

Recommended for You?

Phileas: Would you do something like this again?

Charlie: No, I wouldn’t subject myself to daily dates. It was like a Groundhog’s Day nightmare for me, but one that I felt I had to see through! I don’t regret going through it once though.

Phileas: I can’t imagine going through something like that again. It was really tough on my mind, my heart, my time, and my wallet.

Charlie: Would you recommend this experiment?

Phileas: I think it’s something everyone should do once in their lifetime. But I wouldn’t necessarily tell others to do exactly what I did, just find their own challenge.

Charlie: I would recommend it to those who have abundant curiosity and a really thick skin!

Phileas: Do if for self-discovery, not for finding a mate. The journey matters a lot more than the destination.

—
By Charlie and Phileas (guest contributor).
Photography by Beverley Goodwin

Tags:  dating