Boston, United States
Jenni, 40
Brand Manager
see her Boston city guide

ask Jenni about

historic sites breakfast and brunch brasserie tex mex upscale restaurants cocktail bars gastropub

What do you do and why do you do it?

My entire career has been working in Brand Management for ad agencies. From luxury hotels to baseball hats, beer to insurance, vintage boats to cat food - you name it, I've probably sold it. In my job you get to see and touch all sides of the business - the creative side dreamed up by art directors and copywriters, and the business side that ensures our clients' success.

You’re broken hearted - what tracks does your heartbreak playlist consist of?

Thanks to my husband it's been a loooooooong time since I was broken-hearted ;-) but I do remember one break up road trip with a lot of Fiona Apple.

What are the best TV shows of all time?

If you are a sci-fi nerd there is only one answer: Firefly

Name some spots in Boston that are good for a Tinder date.

Also thanks to my husband, happy to say I live a Tinder-free life but I'd say Sweet Cheeks in Fenway because A) fun ambience, B) solid beer list and excellent BBQ menu, C) your food arrives super fast, ideal if your date is going downhill fast, and D) if it's a total train wreck, you can peace out and meet your girls 2 doors down at Tiger Mama for tiki cocktails and "what was I thinking?" venting.

What’s the area/ spot in town you’ll never be caught dead in?

I'm sure I'll catch hell for this but I am not really into Somerville. Too crunchy for me ;-) My POV may be tainted by being stuck underground on a broken Red Line train one too many times.

What’s the thing you LOVE to do in your city that you never get to do?

Fruit picking! Probably because I don't have a car. When I first moved to Boston I was religious about hitting all the seasons (strawberries, peaches, apples) but now it's been awhile. Few things more classic New England than fall apple picking!

What’s the most decadent / extreme dish you ever ate in Boston and where did you get it?

The epic omakase tasting menu at O Ya. Our 10-year anniversary x 17 courses = 2.5 hours of unforgettable sushi.

Where can you get the best cocktail in Boston? Which one do you like?

Huge fan of the cocktail program at Eastern Standard. Excellent interpretations of the classics plus inventive new drinks. I really like The Phoenix (egg white cocktail topped with lemon ash) but it takes awhile to make so don't be a dick and order if it's crazy busy. Bonus: make it a trifecta with a cocktail at sister spots Island Creek Oyster Bar and The Hawthorne, right next door.

Where would you take your partner in Boston if you wanted to really pamper them?

A romantic dinner at Chef Barbara Lynch's Menton, over the most decadent of chef's tasting menus (since we've already conquered O Ya).

Which snacks can you only get in your country, and which ones do you recommend?

Can you get pickle chips outside the U.S.? Potato chips with the flavor of dill pickles. If you don't like pickles, you're gonna hate these :-)

What’s the one place you think is overrated in Boston?

Much has been said about Drink, a cocktail bar with no set menu where the mixologists will craft something special for you based on your likes/dislikes. If you're a cocktail newbie or need guidance: great. If this isn't your first cocktail rodeo: not worth the wait (which snakes out the door, NOT ideal during Boston winters).

What are the Boston spots a first-time visitor can’t miss?

It's a classic for a reason - the Freedom Trail. Ok it's not a "trail" per se but rather a 2.5-mile outlined route connecting 16 historically important sites in the heart of Boston. Best way to cover a lot of (historical) ground across a relatively short (actual) ground. Immerse yourself in the history of the American Revolution at your own pace and style - whether you want to study the gravesites of every Founding Father or just relax over a pint at Paul Revere's former stomping grounds, The Green Dragon Tavern.

What’s your favorite vacation city in the world and why?

I heart Paris. The sights, the tastes, the vibe - it never gets old. I'm equally happy revisiting my faves in the Louvre as I am whiling the afternoon at a café.

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Michaela Menard