I’ve had many ups and downs in the dating world. Keeping it simple and going slow, from step one, is crucial. So is planning and the right locales. So here’s a start for those in need.
Icebreaking
The drinks date (coffee or cocktails) is a safe first time out. Westport’s NEAT, featuring adult beverages of both kinds, is perfect for this, as you may graduate from coffee to booze (and it’s less hectic than, say, Match). For the more purely caffeine-driven, Stamford’s Bonjo is a go, though Lorca’s ideal for an afternoon pep-me-up sitdown. If it’s a nighttime date, take a cue from New Yorkers and go out on a weekday: less people, more privacy. Norwalk’s Washington Prime is good for this – it’s new and fresh – and always open late (happy hour means half-priced drinks, small plates). LOCAL, nearby, has similar deals, too.
Gearing Up
The “activity”/ “walking” date usually means a nice stroll. In Norwalk, an enclosed path runs parallel now with West Avenue; or try Flax Hill Road, from Jordan’s II to Darien, a beaut of a boulevard. Generally speaking, Darien is unfailingly scenic, as is Rowayton’s Pinkney Park, and while Stamford is a city, it also features amazing revamped parks, such as Scalzi, as well as the Bartlett Arboretum. A truly romantic spot is the walkway along the Saugatuck by the Westport Public Library (think twilight). It’s notable for its seaside dining/drinking proximities should things go well (see below). Oh – and if you want exertion, a purely smashing time, give Bowlmor Lanes in Norwalk a try: It’s pretty amazing on weekends, with a DJ, cleverly constructed cocktails, 2 a.m. closing times and a 21-and-up only crowd.
Settling In
The “dinner” date offers many options (note: a movie date works better later, trust me). You may have your own spots, but I favor Arezzo in Westport for Italian, primarily because of its incredible waterside patio. Hit Bartaco after, then stroll across the river with the flags in the breeze and sit by the library…wow, you’ve made a memory! If you can sit outside at the Little Barn, up the road, book it: Its atmosphere is nice. But as, ahem, cheesy as it sounds, the Melting Pot in Darien also is a lovely dinner date spot, although this informal dating diner has found decent success with Burgers Shakes and Fries nearby. If you are intrepid (try not to recall “Along Came Polly”), Thali in New Canaan has some of the finest Indian cuisine there is for date nights. The less adventurous may find many options, from Greenwich to Westport, at Z Hospitality Group’s various establishments also. They are extremely accommodating for a night out dining, especially Norwalk’s Mediterraneo, within Hotel Zero Degrees, with its fab lounge area. Happy hour there, from Monday to Thursday, is wonderful, with great food.