Let’s talk about sex
…someplace where no children are in sight. A sultry, not-too-noisy wine bar like Webster’s (1480 W Webster Ave, 773-868-0608) will do, but a few drinks at intimate cocktail bar Violet Hour (1520 N Damen Ave, 773-252-1500)—preferably early in the night or on a weekday to avoid a wait—might make pillow talk flow more freely. And in this no-cell-phone zone, there’s at least the safety of not having a call interrupt a tricky conversation.
Breaking up is hard to do
…especially in public. Why does this always seem like a good idea at the time? If you’re sure this is the end of things, go for a sunny, no-booze locale like Café Ballou (939 N Western Ave, 773-342-2909), a quiet, low-traffic coffee shop where you can calmly and patiently explain the situation. But if regrets come easily, pick a restaurant so loud you can pretend your S.O. completely misunderstood you, such as The Publican (837 W Fulton Market, 312-733-9555).
Wedding bells are ringing
…but not if there are a bunch of sullen already-married couples around, mourning their youth over plates of salmon. For one of those DTR (define the relationship) conversations, try for a romantic BYOB (you can bring Champagne) with a youngish crowd, like HB Home Bistro (3404 N Halsted St, 773-661-0299) or Tango Sur (3763 N Southport Ave, 773-477-5466).