Why Not Boston – Episode 2 Teaser from Why Not Boston on Vimeo.

Whether you’re on the best date ever, still trying to figure someone out, or going absolutely nowhere fast, you may as well enjoy yourself (and your city) while you’re at it. Here are some date ideas we totally think you should try with your part-time crush or full-time lover in Boston.


The date: How Hookup… conduct some old-school star searching at an open observatory night at Boston University followed by drinks at Eastern Standard.

Why it’s great (according to Trish): Telescope or not, the view is pretty amazing from the Coit Observatory at BU. You can brush up on your constellations to impress your sweetie or let the BU Astrology Club do the talkin’. As for Eastern Standard, you can’t really go wrong with a place that makes their own infused liquor. The cocktail list is consistently praised by both sexes (no froufrou BS here), and they also carry a top-notch, albeit limited, beer list. If you find yourself starting to trail off from the liquid dinner, they have a fantastic and affordable late-night menu.

Want to go? Click here.


The date: How Hookup… grab dinner at Emma’s Pizza, followed by an independent film at Kendall Square Cinema around the corner.

Why it’s great (according to Lex): This is your casual dinner-and-a-movie night with a bit of twist. At Emma’s, you can enjoy delicious, affordable thin-crust pizza that doesn’t immediately make you want to take a nap. They even give you a choice as to what kind of marinara sauce you’d like (the rosemary sauce is spectacular). The place is a bit small, so leave yourself enough time to wait a few minutes potentially, but it’s totally worth it. And at Kendall Square Cinema, your movie-watching experience is a bit more old-fashioned, not so showy like the big-movie theater chains. Not your average pizza, not your average (limited) selection of films. You’ll leave feeling well-fed and inspired.

Want to go? Click here.


The date: How Hookup… taste-test 250 wines at Second Glass’ Wine Riot.

Why it’s great (according to Trish): There actually isn’t any rioting, unless maybe they run out of something like the 2020 Giorgio & Gianni Lambrusco (the crowd favorite from last year). And it doesn’t matter if you consider yourself a wine n00b or a connoisseur, there’s truly something for everyone. Wine Riot offers crash courses, where local wine buyers and folks form local wineries drop their knowledge on everything from how wine is made to what you should drink with certain foods. There are also food pairings (all under $5), jams to boogie down to, and a photo booth to get your your laugh on with ‘staches, glasses, and hats (oh my!).

Want to go? Click here.


The date: How Hookup… visit Trident Booksellers and Cafe for lunch and a little book browsing..

Why it’s great (according to Lex): This place will charm the pants off you. Who doesn’t love a bookstore attached to a cafe on Newbury Street with outdoor seating? You can grab lunch or stop in for coffee or a supplement-enriched smoothie. Why not? And when you’re done, you can browse books together, which is great for exactly two reasons a) if it’s still early on, you can see what kinds of books your boo is drawn to (and decide to judge or not judge) and b) flirting in bookstores is hot. It’s kind of like that bookstore scene in When Harry Met Sally when Harry checks out Sally while pretending to read a book on Personal Growth.

Want to go? Click here.


The date: How Hookup… hit a concert (or two?) during the Rock ‘n’ Roll Rumble.

Why it’s great (according to Trish): If you find out your cutie is into local music, woo them by buying tickets ($9) to opening night for the first date or get in it to win it by buying a full nine night pass (count ‘em, 24 bands)! (The 2020 Rumble runs from April 3 to April 22.) And if you have a sweet, sweet time at that first concert, you could technically have eight more dates in your future! See how I’m thinking ahead? Plus, who doesn’t want their “how we met” story to start off with, “Well, it all happened at the rumble.”

Want to go? Click here.



The date: How Hookup… soak it up at the Inman Oasis hot tubs in Cambridge.

Why it’s great (according to Lex): Sometimes it’s important to turn things up a notch. Say, if it’s the middle of winter in Boston or if it’s still a very cold day despite it being technically spring. Or if you and your boo need to relax. Or if you’ve been thinking a lot about how great hot tubs are and how much you miss them because you’ve been watching a little too much of The Bachelor where there is always a hot tub handy. You can purchase time in a private two-person hot tub for a 30-minute soak ($40), 45-minute soak ($50), or hour-long sessions ($60). There’s also a community tub which you can enjoy for even lower prices. Go ahead, get out of your head Boston and into the tub! Your boo (and your body) will thank you.

Want to go? Click here.

Trish Fontanilla and Lex Schroeder co-host a little funny web show called Why Not Boston. Watch what happens, and then propose a date here!

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