Actress Gillian Jacobs is well-known for her carefree and sometimes reckless character Mickey on the Netflix show Love. (She also plays a partygoer who is eager to shed her corporate constrictions in the film Ibiza, which is out today on Netflix, as well.) But while the actress might take on characters who hit the town hard, Jacobs leads a very different life offscreen: She describes herself as a “homebody” and as the “first one to go home.” While this early-to-bed approach has fared well for her in recent years, it was not the most effective strategy for going out or meeting guys during her early 2000s college days in New York City. To make matters more complicated, Jacobs, unlike the women she plays, does not drink.

In this episode of Vogue’s Sad Hot Girls, Jacobs recalls how she was invited out to meet friends and be set up with a boy at a Lower East Side bar. To get excited at the prospect, as well as prepare for an all-nighter, Jacobs drank Red Bull. Lots of it. (“Fuck it, I was going to stay up all night,” she says.) And when she mustered up the courage to interact with the guy? Let’s just say her literary pick-up lines weren’t the sexiest. But, as always, there was also a glimmer of hope in the awkward mix. Maybe, just maybe, she ended up with the guy. After all, her mention of Rings of Saturn could have very well been a turn-on.

Here, Jacobs describes how she navigated sober flirting and a very caffeinated night out.

Gillian Jacobs in: 6397 PJ Top, Gap tank top, Pleats Please Issey Miyake shorts, and Tabitha Simmons shoes; Gimaguas bracelet and Céline sunglasses; Batsheva top, Gap jeans, Mari Giudicelli shoes, and Tohum bracelet

Director: Zoe Lister-Jones

Fashion Editor: Alexandra Gurvitch

Story Editor: Liana Satenstein

DP: Arlene Muller

2nd Cam: Erin Naifeh

Hair: Anh Co Tran; Makeup: Molly Greenwald; Manicure: Kimmie Kyees

Set Design: Coryander Friend

Sound: Kara Johnson; Editor: Jesse Threatt