1. Pleasant House Bakery
A casual, inviting meet-up spot is an essential for any online dater, and you need to add Pleasant House Bakery to your list of standbys, ASAP. It’s a bit out of the way, but absolutely worth it — their food is pretentious gastropub quality with British-mother-cooking-in-her-kitchen comfort. Dressed up or dressed down, you’ll hardly feel out of place. The owners are welcoming and friendly, so in sum, you'll feel relaxed and at ease, exactly the way you want to feel when meeting someone new.
Pleasant House Bakery, 964 West 31st Street (at Keely Street); 773-523-7437.
2. Hot Chocolate
Hot Chocolate is a no-fail destination for dessert and hot chocolate (and warm brioche
doughnuts!). I practically panicked when this place closed for renovations, but
they re-open today, just in time to sweeten up summer romance.
Their desserts are a shareable size (hint, hint) and absolutely amazing. Change up
the usual post-dinner drinks routine, or just spike your hot chocolate with a little
Hot Chocolate, 1747 North Damen Avenue (at Willow Street); 773-489-1747.
This is a classic, laid-back summer dinner spot. Moody’s has been
around forever (since 1959), and their brick-walled beer garden and char-broiled
burgers explain why they’ve
been able to stick it out for so long. The summer cocktails might have something to do with it, too. The vibe is chill, the food is delicious, and they’ve consistently earned “best burger” and “most romantic spot” awards from local authorities. Find out for yourself and make the trek up there — even if the weather’s not
beer-garden ready, their indoor dining room is also great.
Moody's Pub, 5910 North Broadway Street (just South of Thorndale Avenue); 773-275-2696.
If you'd like a proper cocktail to take the nervous edge off the first meet, try Bernard’s Bar. This quiet, upscale spot makes some of the best drinks in town. I discovered this place last year and still make frequent appearances. The atmosphere is your (rich) grandpa’s leather and mahogany living room, the music is soft, and the potato chips are freshly made. And, thanks to the diverse crowd (if there’s even one,) you’ll feel at ease in anything from a cocktail dress to jeans and some cool kicks — no pretense here.
Bernard's Bar, 11 E Walton St # 1 (at State Street); 312-646-1300.
Every girl needs her go-to place, or at least a go-to guy to give her such a place. Enter Marc Rochman,
founder of the Epic Date, the first person I call when I need help planning my dates (clients’ and my own!). Marc’s suggestions never fail to amaze, so when he described this place as the “best wine bar in town,” I knew I had to give it a shot. No disappointment here — there are 20+ glass pours so you can try what you’d like, and, if you or your date get hungry, small plates, cheese, or
desserts to choose from. Bon appetit!
Telegraph, 2601 North Milwaukee Avenue (at Kedzie Boulevard); 773-292-9463.
Melissa Malka is an executive dating coach (nationally) and matchmaker
(Chicago & South Florida). Her company, JALBC, focuses on bringing the
science of dating to the surface and helping singles find exactly the kind of
relationships they want to have.