Bay Area/ San Francisco/ Retail & Industry
Published on February 11, 2017
The Castro's Best Date SpotsPhoto: Simon/Flickr

We’re getting those pre-Valentine’s Days jitters here at Hoodline, neighbors. And while we can’t make you more dateable by waving a magic wand over your love life, we can recommend some neighborhood date-spots for you to consider.

1st Date: Coffee, Wine, or Dive

If you’re always dragging your first dates to the same bar, sit at the same table, and order the same thing, it’s time to shake things up.

When it comes to first dates, we all have our preferred setting, time of day, and ambiance (not to mention noise level, drink of choice, and escape plan).

If you like to blend your first dates with something caffeinated, we recommend Hearth (3985 17th St.). There’s plenty of seating, ample natural light, and if things go well, the coffee shop has a food menu to complement its beverages.

If you prefer to meet a person for the first time with a glass of Pinot Noir in hand, consider heading to Blush! Wine Bar (476 Castro St.). With a relaxed, welcoming atmosphere, Blush! is a great place to leave your pre-date jitters at the door and have a nice conversation.

Or if you’re looking to keep it casual (and cheap), head to the Pilsner Inn (225 Church St.). It's rarely packed, there's a pool table, and the bartenders are lovely—need we say more?

Photo: drufisher/Flickr

3rd Date: Competitive Much?

So, things are going pretty well between you and your new squeeze–congratulations. Now, it’s time to figure out how competitive each of you are.  

Take an evening and mosey over to Brewcade (2200B Market St.) to kick back with some quality draft options and vintage arcade games.

Whether its driving race cars, hunting bighorn sheep, or channeling your inner Ms. Pacman, chances are you’ll learn something new about your new flame.

Plus, if you get hungry, you can always walk next door to Hecho Cantina (2200 Market St.) for some nachos.

Double Date: Head for the Hills

If you spend all of your time in the Castro, consider packing a lunch and gaining some elevation the next time you plan a double date with your couple friends.

We’d recommend grabbing some sandwiches from Rossi’s or some burritos from Zapata’s (we all have our preferred to-go grub here), and climbing to Corona Heights.

Photo: Shane Downing/Hoodline

The thought might seem daunting (to your friends, not to you), but the views of the Castro and surrounding neighborhoods make the shortness of breath worthwhile.

If you’re feeling super sporty, you could then risk the Iron Stairs to Twin Peaks for even more stunning vistas.

Anniversary: Castro Theatre and Chill

As you’re celebrating your whatever-year anniversary, make sure to also take a moment to celebrate delicious California cuisine. And nothing says “happy anniversary” quite like a meal at Frances (3870 17th St.). The menu changes based on seasonal ingredients, but the cozy environment and good vibes remain the same.

After your meal, we recommend paying a visit to the Castro Theatre (429 Castro St.): one of the best places to celebrate companionship.

Photo: Shane Downing/Hoodline

Breakup: Surround Yourself with Sweetness

Breakups are never easy, but if you’re going to breakup with someone, do it around around the cakes, cookies, and ice cream of Sweet Inspiration (2239 Market St.). It’ll be easier for you and for your now ex if each of you has a slice of comfort to savor as your relationship crumbles around you.

(Pro tip: Don’t sit at one of the tables at the front of the bakery, near the windows, unless you want to make a scene.)

Where's the best place to be broken up with?

If it were up to us, we'd say Hot Cookie (407 Castro St.).

Think about it: you can say goodbye, grab your cookie, convince the guy behind the counter to leave his shift early, and retreat to literally any bar on the Castro's main drag.

We never said that first dates couldn’t be made up on the fly.