40+ Matched Speed Dating in Fenway, Ages 40-55

New Venue Alert!

Ditch the apps and meet real singles in person as CitySwoon comes to a great new venue, Trillium Fenway!

Join a big room of singles and get around 8 of your best live-selected, mini-dates!

Meet like-minded singles face to face in a relaxed, fun and social atmosphere.

Spots are limited, booking is essential.

How it works:
- Quick check-in on your phone. No nametags, matchcards, pens or fuss.
- Loads of singles in the room. Our platform finds your best matches for each round of mini-dates.
- Friendly, professional hosts guide the night.
- Balanced mix of men & women so the event flows naturally.
- Stay and mingle afterwards, most people do!

Why you'll love Smart Speed Dating:
- Relaxed, social vibe, perfect if you're coming solo (most do!).
- Great venues, great people, and actual conversations.
- Over 95% of attendees meet someone they're attracted to, and 90% get at least one mutual match!
- 10+ years of successful CitySwoon events and millions of dates!

Learn more about CitySwoon and our unique events on the
FAQ page.

The Venue

Trillium Fenway is a modern, greenhouse-inspired taproom and outdoor beer garden located at 401 Park Drive in Boston's vibrant Fenway neighborhood. Trillium is highly popular for pre-game drinks before Red Sox games, after-work hangouts, and weekend gatherings.

All our venues are carefully selected for great vibes and atmosphere.

Tickets are non-refundable.
You can cancel 7 days out and receive a credit or transfer.
A $19 late cancellation/no-show fee applies if you cancel within 24 hours of the event.
See Terms & conditions for details.

Ready to meet your match? Grab your ticket today, spots go fast!

NB: A fully completed CitySwoon profile, complete with a profile photo where your face is clearly visible, is required to fully participate in any CitySwoon event.