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.
BACHELORS and BACHELORETTES: Hayley | Mark | Josh | Casey | Caitlin | Jordi | Claudiane | James | Christina | Sam | Matt | Titi | Caroline | Kitzner | Elizabeth | Garrett | Michael | Alex | Chrissy | Derek