100 First Dates

A few years ago, my friend Lisa started a project about dating.

After all, Lisa was a super successful New York gal in her thirties (cue every rom com trailer ever) and after a failed relationship, she was ready to put the whole dating thing to the test. 

Lisa's project was called 100 First Dates. The idea was that she would go on first dates with 100 men, but if anything worked out along the way she would stop the project and just date the guy.

It never did. Lisa went on all 100 first dates, and if that doesn't tell you something about the New York dating scene then I don't know what will. It's a cliché but it's also true – had I not met D, who was visiting town from another country – I think I'd still be single today.

Lisa finished the 100 First Dates project last year, and is now turning it from its original form of a blog to a comedy show and podcast, amongst other things. 

Because Lisa is awesome and my friend, and because I genuinely think there are some crazy things going on with modern dating, I asked Lisa some questions about 100 First Dates. 

Here, girlfriend spills on her experiences with dating and relationships – 

How do you describe 100FD? What's your bite-size, cocktail party definition for the project?

You know how most women between the ages of 32 and 36 get married and have babies? I went on100 First Dates instead.

After my ex-almost-fiancé broke up with me unexpectedly, I “got back out there” and acquired some really great, ridiculous dating stories. Writing them down became a creative and cathartic outlet. My goal was always to find love, but I haven’t yet so here I am 100 and counting…

At the start of 100FD you were anonymous. Now, your name is everywhere. Why did you decide to "come clean" about the project?

For a long time I thought I could – and should – keep my blogger self separate from the “real” me. I felt fearful that guys would be scared off and wouldn’t want to date me.

Now that I’m older and wiser, I’ve come to realize (and be proud of) this project because it's a huge part of who I am. I’m a writer, a comedian, and a very open person. If a man is frightened by all of that, then he isn’t the right guy for me.

When you were on dates did you have trouble separating Lisa, blog writer and project creator, from the "real" Lisa?

When I could feel a date take a turn for the worse, the only thing that helped me cope was the knowledge that I could write about it. I took my bad experiences, made light of them, and basically threw them up in a post.

You've gone on dates with 100 men in New York. Are you any closer to answering the question of why dating is so hard in the city?

The “Next Best Thing” syndrome is definitely a factor. There is always someone else to go out with if the date you’re on isn’t great, and with dating apps like Tinder that next someone else is easy to find.

People in New York are ambitious. They’re hustling in this city for a reason, but that reason is never to find a life-long partner. As a result, people are distracted during the prime mating years because they’ve got careers to find and dreams to fulfill. They tend to settle down when they’re older, which is dandy for men because they don’t have biology banging down their doors. For women, it’s different.

Biggest lessons learned during your experience?

Take risks! Meet people online AND offline. You may not find the right person right away, but you will learn about yourself and meet interesting, smart, funny (and weird) people that may surprise you. It’s all about getting outside your comfort zone.

Other key lessons:

  • Text to make plans not to make conversation – that’s where the weirdness happens.

  • Plan for a first date drink, not dinner. Dinner is harder to escape.

  • Find a sexy, comfortable first date outfit and wear it on every first date.

  • If the date isn’t going well, be respectful and honest, and get out of there!


You've gone on your 100th date. What would you like to happen next with this project?

I would love to write a book about my experiences and lessons learned.

After that? I’ve been so touched by blog readers from all over the world who’ve reached out to me that I’ve learned that love and heartbreak are truly universal. My dream project is to travel around the globe to talk to men and women about what dating, love, and relationships mean to them, and to document it in a book or on film. If anyone has any other ideas, send ‘em my way! 

Thank you, Lisa! 

Learn more about 100 First Dates here

Contact Lisa here

Follow Lisa here and here