At Tosca, the bar is where it's at: stellar drinks, stellar bartenders, and stellar vibes. Just be sure to arrive a little earlier than your date to do the chivalrous thing and secure some seats for the two of you (you can even sneak in a loosen-up drink) — nothing is worse than pretending you love to stand while trying to romanticize a stranger.

The name of this quirky, hipster coffee shop is not an exaggeration — it's a literal hole in the wall — but the coffee is great, there are real coconuts for the buying (which can be a fun, if confusing, alternative to coffee), and it's right near Washington Square Park, which has top-notch people watching for bonding moments.

There may be no more perfect a meal than pizza, pasta, and wine on a second date, and Cotogna leads San Francisco in those three categories. The lighting is always just right, too.

Kokkari is a special occasion classic for a reason: It consistently nails the restaurant holy trinity — food, service, and atmosphere — with its wood-fired Greek food and attentive staff.

Live jazz in a supper club setting is just what you need to add romance into a date, and Bix has both (plus tons of whiskey) in spades. The menu of American classics with modern twists always impresses.

A karaoke bar may seem an odd choice for a breakup spot, but the more you think about it, the more genius it becomes. There's plenty of music to drown out any of the more heated moments in your conversation, people are too focused on the singer to notice you, and you can even sing a swan song if needed.