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Rainy Day Casual Date Tips (From a San Diego Company Who Honestly Forgot Weather Was Even a Thing)

BCU November 18, 2025

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Did you know? OBC is headquartered in sunny San Diego, the land of rooftop lounges, ocean views, and bars specifically designed for people who want to flirt while holding a drink and a tan. So you can imagine our collective shock when the skies opened up recently and reminded us that apparently… it rains here. Who knew.

Rainy weather takes our usual date spots off the table. No beach bars, no sunset strolls, no rooftop cocktails with the perfect golden-hour lighting. But rainy days can actually make for some of the best dates, especially if you’re down to keep things casual, cozy, and low pressure.

Here are a few rainy-day date ideas to turn those gray skies into something a little more fun.

1. Go somewhere with great people-watching.
Cafes during a storm are peak entertainment. Order something warm, grab a window seat, and watch people sprint through puddles like an Olympic sport. It’s lighthearted, it’s relaxed, and you can learn a lot about someone by how they react when a dog in a raincoat walks by.

2. Try a “two-stop date.”
Pick two walkable indoor spots and hop between them. Maybe a bookstore, then a wine bar. Or an arcade, then tacos. The short dash between places in the rain adds just the right amount of rom-com energy, but without any sap.

3. Lean into cozy chaos.
Find a bar with dim lighting and comfortable chairs, something that feels like the adult version of a blanket fort. Order shared appetizers, talk about life, and let the rain soundtrack do the flirting for you. It’s easy, laid back, and way better than yelling over a DJ on a rooftop.

4. Do something hands-on.
Pottery studio, cooking class, painting bar. When the weather kills the beach vibe, shift to an activity that gives you something to do with your hands and something to laugh about later. Bonus: you’ll learn quickly if they’re fun, chill, or secretly competitive.

5. Use the rain as an excuse to keep things short and sweet.
A rainy date is the perfect one-hour meetup. Grab a drink, see how it feels, and dip (literally) if it’s not sparking. Or extend it if the chemistry is unexpectedly warm. Low pressure, high potential.

If you want someone to share a rainy coffee, a cozy bar stool, or a puddle-dodging adventure with, join OBC and meet other singles who love keeping dating fun, flexible, and drama free.

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