First dates in Highland Park
Two parallel commercial streets that locals treat as two different nights out, a 1927 bowling alley that solves the first-date problem, and the rail line almost nobody uses.
Highland Park has two commercial streets, not one, and that is the thing to know before you make a plan.
York and Figueroa are different nights
York Boulevard is densest between Avenue 50 and Avenue 54. More bars, more vintage, more brunch, and the busier of the two on a weekend.
North Figueroa Street runs roughly Avenue 50 to Avenue 60. More entertainment anchors, more coffee, more spread out.
They are parallel, about half a mile apart, connected by the numbered avenues. You can walk between them in eight to twelve minutes, but it is a real hill, and locals do not treat it as one strip. Pick one. On a map the corridors look continuous; on foot they are not — both have stretches with very little going on between the clusters.
The venue that does the work for you
Highland Park Bowl at 5621 North Figueroa is a restored 1927 bowling alley with cocktails and pizza. It is the best first-date venue in the neighborhood and it is not particularly close.
The reason is structural rather than aesthetic. A first date has one job — finding out whether you want a second one — and the hardest version of that job is two strangers sitting across a table generating conversation from nothing. Bowling removes the problem. There are natural pauses, something to react to, a reason to stand next to each other, and a built-in ending. You learn more about someone in an hour of bowling than in two hours of dinner.
Expect a wait on weekends. Go on a weeknight.
The Lucky Tiki, a tiki bar, is reached through the bowling alley. Having somewhere to go next that the other person did not know was there is a good second act.
The rest of Figueroa
Gold Line Bar is a vinyl-focused neighborhood bar on Figueroa, and the kind of room where the music is the thing you talk about first.
The Lodge Room, upstairs in the Highland Park Masonic Temple near Avenue 56, is a mid-size music venue with a full calendar. A show is a legitimate first date for the same reason bowling is — the evening has a shape, and you both have something concrete to talk about afterward.
York
Donut Friend at 5107 York Boulevard does vegan donuts named after punk songs. It is cheap, it is quick, and it is a good low-stakes daytime meet when neither of you wants to commit to an evening.
The Hermosillo at 5125 York is the brewpub end of the street.
The free standing options
Three run clubs meet in Highland Park weekly and all of them are free:
- Tofu Scramble, Friday 6:30am, from K&M Coffee
- Garvanza Run Club, Sunday 8:15am, from Garvanza Park
- Slow Runners LA, Sunday 9am, from Delicias Bakery
The last one is named accurately, which is the point. If the idea of a run club is intimidating, that is the one.
Transit, and the thing nobody does with it
The Metro A Line stops at Highland Park station at Avenue 57 and Marmion Way, about three blocks off North Figueroa. Since the Regional Connector opened, that is a single ride to Downtown, to Pasadena, and all the way to Long Beach.
The useful version of this: Highland Park to Old Pasadena is about fifteen minutes on the train. You can meet someone halfway between two neighborhoods without either of you driving or parking, and essentially nobody plans dates this way. It is the best cross-town corridor in the city and it is sitting there unused.
Parking and the honest downsides
York fills up Friday and Saturday evening, and the side streets off it have permit restrictions. Figueroa is generally easier because the businesses are further apart.
Two honest notes. Gentrification here is a live local conversation, and a night out framed as discovering a cool new strip lands badly with people who have lived here a long time — it is worth being a guest rather than a tourist. And the weekend crowd on York skews noticeably homogeneous; if you want more variety in the room, Figueroa is the better bet.
If you want one plan
Weeknight: bowl at Highland Park Bowl, then the Lucky Tiki if it is going well.
Weekend afternoon: Donut Friend, then walk York, then decide.
Something different: take the A Line to Pasadena and meet there instead.
Common questions
- Is York Boulevard or Figueroa better for a first date?
- Figueroa, usually. York is denser and has more bars, but Figueroa has the activity venues — bowling, music, coffee — and a date built around doing something is easier than a date built around talking across a table. They are about half a mile apart and locals treat them as separate nights.
- Can you reach Highland Park without a car?
- Yes, and it is one of the few LA neighborhoods where that is true. The Metro A Line stops at Highland Park station, about three blocks from North Figueroa, and since the Regional Connector opened it is a one-seat ride to Downtown, Pasadena and Long Beach.
- How far is Highland Park from Pasadena?
- About six miles, and roughly fifteen minutes on the A Line. It is the most underused cross-town date corridor in Los Angeles.
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