Perfect walk length even if one of you has uncomfortable shoes. Look nice because why would you not? 3 choices for food so pick one based on vibe.

The Wolves

Bar · Downtown Los Angeles

"I could probably stay out a little bit longer": Anyone who goes here knows the deal; it's cool and impressive and you can take selfies in the bathroom if everything else sucks. But also things usually don't suck here because it's too small to be loud and too nice for anyone to be mad for having gone. The bar stools don't have seat backs but there are some 2 tops with chairs so use that info when figuring out where to try and sit.

Orsa & Winston

Italian Restaurant · Downtown Los Angeles

(Upscale): "This is nice": Look if you need to go to a real-deal sit down restaurant you should go here. It's on the "Places to make your parents pay" list but it's cool food that is also Italian and "asian fusion", probably the two safest categories for the American palette (what is more American than generalizing an entire continents cuisine?). It's also incredibly bomb. The Wolves is not far.

Bar Ama

Mexican Restaurant · Downtown Los Angeles

(Sufficiently nice): "This is fun": Bar Ama is adventurous without being a risk. You will love the food. It's also got a lot going on and it's fun trying to divine what even is Tex-Mex with the other L.A. resident sitting across from you. Good drinks too but like The Wolves is only a couple blocks away.

Guisados

Taco Place · Downtown Los Angeles

(Laid Back) "This is fun": Eating a full meal in front of someone is it's own kind of awkward so imo get in and get out. Drop cash on the drinks if you want but don't overthink food. Tacos are fast (and none of the guisados are particularly vibey aside from the original) so like prove that you can hold and eat a taco cleanly (read: have standards) and get out. The Wolves is next door.

Wyman Bar

Bar · Downtown Los Angeles

"The Second Location": It's new, its cool and it's worth it for the lobby. 4 months after the pandemic is *actually* over they'll make it members only so act fast

Grand Central Market

Market · Downtown Los Angeles

"Can We Talk?": Ya got options here: Is it a prosecco and oyster situation? Straightedge coffee or milkshake situation? The best is to do a lap, talk it over and decide on either one appetizer and one drink at once or a mix and match tapas deal. Talking too much/less and need to switch up without awkwardness? Ask about another round of food or drinks instead of whether you should leave. Sometimes the vibe is perfect. (Oysters, Nam Tok at sticky rice or the octopus tostada at Tostaderia )