a co-worker is getting engaged in december and has asked me for a few recc's on restaurants.
the couple is in their late 20's, maybe early 30's, and not very up to date on the Boston chow scene.
i want to steer them to a place that is not too loud and has a nice, but not imposing feel.
i think the food should be simple and straight forward and a staff that isn't too snooty for folks that don't order on the cutting edge.
i want parking to ba a non-issue so a lot or valet is a must.
that said, my current thinking is either Mamma Marias, with a nice window seat overlooking the square, or, Ruth's Chris, for the room and familiarty of the food. i was also thinking Mistral because i think their current menu would be approachable. i would not reccommned Clio, Radius or any other gastro-delightful places as i feel the food, if they even understood it, would overshadow the occasion.
I'll bet the question gets popped at L'Espalier multiple times a week, but it falls down on a lot of your other criteria.
I think Pigalle might fit the bill: it's intimate and romantic, special-occasion feeling, but not intimidating. I'll bet if your friend had a conversation with their extraordinary hostess ahead of time, she'd make it pretty special, get him a nice corner banquette and so on. I think Rialto might work, too.
Other quietish, romantic places that aren't too over-the-top might be Salts, Troquet, Fugakyu (in one of their screened-in booths, maybe), Lala Rokh, a tent table at Tangierino. Icarus is a very pretty room, and the lower half of the dining room isn't too loud if it's not packed.
It's a fun problem.
Maybe Aujourd'hui? I don't know how "fancy" the current menu is, but I don't recall it being too over the top. The service was lovely (not snooty) and the place feels very 'special occasion' to me.
ETA: The lights should be on in the common by then, which could be a nice pre-or-post dinner stroll, if it's not too freezing.
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After writing this, I realized that you may be looking for a place for them to get engaged, not for an engagement party. If that's the case, I still think Mistral is a good choice, but I'll leave my post here anyway in case anyone is interested in a good place for a party!
I did two functions at Mistral over the summer, and both were extraordinary. Although they offer other options, the option I chose for both functions, at a cost of $100/person (not including beverages), includes a choice of five passed hors d'oeuvres, an appetizer, three entrees for guests to choose from, and a dessert (they have one choice that is a trio of desserts and includes a chocolate pot de creme, a creme brulee, and a warm chocolate cake; IMHO this is the best option). For our entree options, we chose Mistal's rack of lamb and half duck -- both of which they consider to be "signature" dishes -- and a halibut dish. When I asked after the party, I was told that guests had ordered the entrees in nearly equal numbers. Also, they did a great job of accommodating special requests, including vegetarians, dieters, and kids (for whom they brought a bunch of pizzas; Mistral makes great pizzas, and a lot of the guests were stealing pieces from the kids!). And although Mistral has a wonderful wine list, they worked with me to choose more reasonably priced bottles for the parties.
The Salon Room is beautiful, the service is extraordinary (ask for Jeff and/or Tarso to work the party), and all of my guests were wowed.