Everyday Icon: The Single Lady

Blogger and comedian Lisa Pertoso of "100 First Dates" gives us a look into her dating history and what has emerged from all those romantic experiences.

It sounds like an urban legend, or maybe even a vintage newspaper headline: Girl gets dumped by boyfriend, dates 100 men in New York City. But, Clementines, this isn’t an urban legend – this is the story of Lisa Pertoso’s 100 First Dates project. After a failed relationship left her single, Lisa opted to take the high road rather than wallowing in her stress and started a blog that takes a close look at the modern dating world. The blog has now become a podcast and an improv comedy show – and Lisa’s only getting started. We were lucky enough to talk to Lisa about her project and are so pleased to share it - whether you’re single, or just need a shot of can-do optimism, this is one for you:


The name of your project, 100 First Dates, is pretty self-explanatory, but since you started, it’s evolved greatly. Tell us about the origins of the project, and how it’s become what it is today.

After my ex-almost-fiancé broke up with me unexpectedly, I “got back out there,” began dating, and soon acquired some really great, ridiculous dating stories – it is New York, after all. Writing about my experiences became a creative and cathartic outlet.

That purpose of the project has remained the same, but my expectations have definitely shifted. I (naively) assumed when I started the project that I’d find real love pretty quickly, and I was wrong. Instead, I found my real self and a real love for comedy along the way. I focus more energy now on my relationship with myself.

Why did you decide on specifically 100 dates?

One of my strengths (and perhaps a weakness) is that I love challenges and don’t like to quit. I also like good titles and round numbers.

You started the project anonymously, but you’re now open about who you are. Was the anonymity at first related to keeping truth in the project, or protecting your private life? How did you make the decision to go public with your identity?

For a long time I thought I could – and should – keep my blogger self separate from the “real” me. I feared that guys would be scared off and wouldn’t want to date me. I also feared I wouldn’t be able to tell the whole truth if I knew the person I was on a date with would be later read the post about our date.

Now, I’m older and wiser I’ve realized this project is a huge part of who I am and I’m proud of it. 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.

With creative projects, there’s often a struggle in separating the person from the project. The struggle for you must have been even more difficult because your project is based on your personal life. How do you separate Lisa, the blogger, dater, and comedian, from Lisa, the person?

I can’t – it’s too late!  I believe (and hope) that people read 100 First Dates and relate to it because I consistently put myself out there.

You’re now crossing between the worlds of online publishing, comedy, and podcasting. Are there any particular writers, comedians, or podcasters you look up to?

I’m obsessed with Kristen Wiig because she’s beautiful, funny, a talented comic and writer, and she’s about my age. I admire the risks she’s taken to cross over into dramatic acting because I don’t think I could do that. My favorite podcast in the world is The Moth, because true stories are always richer, funnier, and more touching than fiction for me. Speaking of storytelling – Louis C.K.’s stand up really speaks to me because most of his jokes are short stories, and there’s something about that format that I find really interesting.

Now that you’ve seen what’s out there, have your feelings about relationships changed at all? Are you more or less hopeful?

Some days I want to crawl back into my little apartment, turn on Netflix, and hide under a blanket. Other days I’m awed by the interesting people I’ve met, the connections I’ve made not only with my dates, but also with my blog readers all over the world. We’re all looking for love and going through the same challenges.

I’m as hopeful, but more realistic. No one is perfect, especially not me. I know now that there are other loves besides romantic love. My friends, my creative projects, my comedy, my friends’ kids, my family – those loves are as important as romantic love if you want to have a happy life.

At Clementine Daily, part of our mission deals with helping women to set realistic expectations and better their lives so they can better the lives of others. Do you feel that this experience has bettered, or changed you in any way?

I’ve grown up a lot. I’m more open, I take more risks and I’m not afraid of failure. I’ve learned the delicate art of self-facilitation, meaning I’m more in touch with my emotions and behavior, and I’m conscious of how they affect other people.

I can only control myself. If a guy acted rude, weird, ran away, broke up with me, I finally, finally, finally understand that it was not about me. There was nothing I could have done or changed. This discovery allows me the freedom to be myself all the time.

Since you started 100 First Dates, how has your experience as a single woman changed? Are you now more confident, or less?

I’m far more confident. I don’t put unrealistic expectations on my dates, and instead only hope to have fun and learn about someone new. Whether the date is good or bad I know that ultimately I’ll be fine. I have over 100 dating experiences as proof.

Fill in the blank. “In five years, my goal is for 100 First Dates to…”

Continue to inspire people to “get out there”.

Continue to make people laugh.

Be a book.

Be a web series.

Be a movie.

Be a funny anecdote that my husband and I tell at parties.

I have no idea and that’s what makes life exciting.

We have to ask: What were your best and worst dates?

My worst dates happened when the guy was rude, selfish, and shared way too much intimate information. Date 19 told me he was online only there to “get laid”. Date 56 did not facilitate himself and took his bad day out on me. Date 66 yelled at me on the street because he didn’t like my choice of subway line to go to my own home. And my personal favorite, Date 99 looked me in the eyes and told me I was the worst date ever before running out the door.

My best dates happened when my expectations were the lowest. Jeremy, Date 61, and I dated for a couple of months one winter and our dates were epic. Long afternoons of cuddling, drinking whiskey, talking for hours. Date 55 and I had a great first and only date walking around my neighborhood grabbing coffee and watching a dog Halloween parade. Date 100 and I had a great time because we only expected to have fun (we did!) and not to fall in love (we didn’t).

p.s. We would love to know: what were you best and worst dates?