PSA: You Should Be Stacking Your Dates With Other Plans

“Anyone want to go to happy hour?” I sent in my book club group text at 4:30 p.m. “I have a first date tonight (allegedly) and want a girly pregame.” I’ve been sending versions of this text since I first downloaded dating apps in my senior year of college. This time, one friend agreed, and we each had a glass of crisp Sancerre before I ran off to meet my date at a nearby dive bar by 7:30 p.m. Slightly buzzed and with “Dreams” by The Cranberries playing in my headphones, I felt light and bouncy on my walk — like the lead in my very own rom-com.

To some, this might seem like an unnecessary step in an already extensive pre-date routine (my personal go-to is a fake tan, hair blowout, makeup, and a $12 tank top that is shockingly flattering). But for me, it makes the prospect of meeting someone new much more appealing. First dates can be pretty meh — you run the risk of awkward small talk, unfortunate catfishing, or complete ghosting, not to mention actual threats of harm. It’s a lot to hype yourself up for, and sometimes, you need a little extra help to get through the evening.

So over years of trial and error, I’ve developed one dating strategy I swear by: stacking your dates with other plans. I’m not alone. TikTokers often tout the benefits of pregaming a first date with your besties or having friends come over for moral support as you get ready. (Even some dating coaches recommend booking first dates back-to-back — Sex and The City’s Charlotte York dabbled in this strategy in Season 2.) If you’re up for adding some buffers into your itinerary, here’s how to orchestrate the technique perfectly.

1. Pick a spot to hang out with friends before or after your date. Friends of mine love a post-date plan: GNO, trivia, or even a late dinner at your favorite spot. Think of this plan as your exit strategy. Hate your date? You can head out early and blame it on bad scheduling. Already have heart eyes for this practical stranger? You can count on these late-night plans to keep you from falling too soon. I typically go for the pre-date plan — I personally believe the mark of a good date is a secondary location, so I don’t want to nix that possibility from the get-go. Plus, Sancerre tastes better at happy hour.
2. Get creative. I’ve stacked first dates with an outdoor happy hour, a tour of my friend’s new apartment, and even a magic show. It’s really the dealer's choice — something as simple as a FaceTime call with your long-distance bestie counts. Just keep things flexible since there’s always a chance you’ll get tied up, either with your getting-ready routine or with flirting.
3. Make the most of your glam. Part of the appeal of stacking your schedule is that you are conserving resources — two outings and only one look! Go for the cat-eye. Take time with your contour. Lip line to your heart’s desire. Pack supplies in your purse for touch-ups as you go.
4. Watch what you drink. I’ve made the mistake of imbibing in a few too many before a date, and although conversation flows more loosely, it also makes it hard to gauge if you actually like the person sitting across from you.
5. Stack a date with another date — only if you want. This is definitely allowed. You’re single, after all. I personally wouldn’t, partially because I refuse to save men’s numbers before a date, so that would be a logistical nightmare. But to each their own!
6. Keep the plans to your inner circle only. You don’t want to drain your social battery right before a date, so stick to people who don’t require too much effort to be around. These friends already love you — a good reminder that at least *some* people enjoy your company before you put yourself out there for someone else to judge.
7. The conversation should be light. Whether you’re catching up before or after a date, avoid heavy topics. I love to chat about the date ahead — where we’re going, how we connected, first impressions (including red and green flags). You can have this same conversation post-date, BTW, just with more details.
8. Text your friends the debrief later. I’m always giving my friends the down-low on my walk home. Rambling voice memos and texts like “he definitely lied about being 6-foot-2” and “he paid for both rounds of drinks!!!” abound. (IMO, it’s the equivalent of studying with a friend before a test and then calling them right after to compare answers.)

I’ve found the biggest benefit to stacking plans is that it instantly takes the pressure off. By adding some stops to your itinerary, the date no longer feels like a defining moment of your life — it’s not even the defining moment of your evening.

So, please consider this my formal petition to retire the phrase “date night.” It may be a night with a date, but you’ve got plenty of other sh*t to do and people to see.