Ask Gabi: “20 Guys You Date In Your 20s”

The guy who got away. The guy who’s hotter than you. The guy you always go back to. The guy who’s much older. The guy who’s toxic. The guy you can’t remember.

Gabi Conti knows them all. She’s dated them all.

Now she wants you to know them too.

Gabi — a 2005 Staples High School graduate — is in her early 30s. But all those experiences happened in her 20s. Hence the title: “Twenty Guys You Date in Your Twenties.”

(The first guy was actually a fellow Stapleite, when she was 16. But he made the cut, because they reconnected a decade later.)

Gabi Conti, with her book.

“Twenty Guys” is not some random collection of thoughts. Gabi began writing at Staples for Inklings, the school paper. At Emerson College she studied broadcast journalism and writing for TV and film.

She moved to Los Angeles, worked as a production assistant for Comedy Central, did stand-up and sketch comedy, wrote videos and editorials, and blogged about her comedic musings.

Starting in high school, she kept a “love journal.” At 23 she had a “traumatic break-up”: The guy she’d dated for a year had been lying all along about his age.

At 29, Gabi decided she wanted to get published before she turned 30. She realized she had all the material she needed. It just needed to be, um, massaged.

She also needed to make sure it was okay to publish. She contacted 19 exes. Some were surprised. But all were fine with her idea. (She changed names and certain information to protect, presumably, everyone.)

She got an agent, and a contract. “Twenty Guys You Date …” was just published.

One of those guys.

It sounds racy. But, Gabi says, “it’s really PG-13. It’s more about relationships than sex.”

In fact, the final chapter is about her parents’ dates (and marriage). Spoiler alert: It does contain a little sex. But just a little.

“Twenty Guys…” is not only for 20-somethings. “If you’re single at any age, this book is for you,” Gabi says.

“You can also change the pronouns, based on who you are and who you love.” Bad dates cross genders and sexualities.

Of course, I had to ask: What’s Gabi’s dating life like now?

After writing her book — but before it was published — she did a “dating experiment” for Cosmo. She went on 30 dates in 3 days.

“I learned really good dating habits,” she says diplomatically. But when that was over, she met a guy…

In September, they went on 3 dates in 3 days. Now they live together.

I did not ask if she’s still taking notes.

(To order “Twenty Guys You Date in Your Twenties,” click here.)

10 responses to “Ask Gabi: “20 Guys You Date In Your 20s”

  1. Daniel Craig

    20 dudes in 10 year span —/.

    Not a badge of courage

    More like a scarlet letter

    • Elizabeth Thibault

      Your comment is cringy and really shaming. Not every date leads to a long and meaningful relationship. Sometimes you can tell after having coffee for 30 minutes with someone, that you’re not going to click romantically. Some people you date turn into a friend instead. We wouldn’t shame a man like this either; this type of judgement is rooted in misogyny that we need to leave in the last century.
      She’s an accomplished young woman who grew up in Westport and has seen significant career growth and success. Celebrate this and lift people up instead.

  2. Richard Santella


    I truly do appreciate the effort you devote, day in / day out, to managing this blog. Visiting this site has become a daily ritual for me in between a morning cup of coffee and getting ready for work.

    That being said, you can do better than this “Ask Gabi” piece…

    • Donna Tannis

      She’s a Westporter, a Staples Graduate and published a book. Get over it.

  3. Jeff Jacobs

    Yes, I’ll take exception to the previous comments, even though I’m not in the ‘target audience” for Gabi Conti’s new book. Yes, it is interesting to learn about what people – particularly, like Gabi, those associated with Westport – are experiencing. Yes, I never cease to be amazed by Dan’s energy and talent (as a reporter and a blog producer) in bringing those diverse interests to our attention in an interesting and informative manner. Bravo (again)!

  4. Cathy Walsh

    Scarlet letter? Are you kidding me? Get a life, boys. Bravo Gabi for being published. Good luck with all your future endeavors.

    • Cathy and Jeff, I second that emotion. This is certainly, to borrow from Elaine Benes, “06880”-worthy.

  5. Jack Backiel

    We all know that when a male and female break up, 97.64% of the time it’s the guy’s fault! Everyone knows this!

  6. David Squires (Staples '75)

    Sounds like a Rom Com Movie, if Hollywood ever makes movies again!
    Pass the Popcorn Please….

  7. Isabelle Breen

    “The guy she dated for a year had been lying to her all along…”
    And you’re shaming her?!?!