Strike a Match

Meet Boston's most eligible singles, class of 2019

It feels like we’ve been sending this annual Valentine—our roundup of Boston’s most eligible singles—to readers for decades. And that’s because it has been decades. Always an interesting group, this year there are pro athletes, entrepreneurs, entertainers and hospitality all-stars. The one thing they all have in common is they’re not currently spoken for—and they have a lot going on in their lives that make them intriguing romantic prospects. So, without any further ado, we present The Improper’s Most Eligible Bachelors and Bachelorettes, class of 2019.

I love people who are either very large in stature or very small. I want to either climb you or put you in my pocket. 

Special skills: I’m conversational in Italian and Spanish—not fluent but still learning. And I try to keep a dad joke loaded at all times.

Favorite cocktail: Gin fizz, because I like the effort, or anything with habanero or jalapeño in it.

Most romantic place in the world: Next to the fireplace, on the couch, under a blanket.

Celebrity crush: Prince Harry—a ginger with good manners. What more could you ask for?

What if your date refuses to dance: We’ll get lessons as a follow-up date.

The most romantic thing in the world: Thoughtfulness goes a long way. Candles, a fireplace, ocean waves and vino never hurt a situation, either.

Awards and honors: In college, I was the president, also known as Queen Gay, of “Studio Q,” our LGBTQ+ organization.

BACHELORS and BACHELORETTES: Hayley | MarkJosh | Casey | CaitlinJordiClaudianeJamesChristina | Sam | MattTitiCarolineKitznerElizabeth | GarrettMichael | AlexChrissy | Derek


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