Flirty Dating Guide for Rooftop Romance

If you've yet to notice, the hottest locals in San Diego are taking the elevator up to rooftop lounges for the ultimate in trendy summer entertainment.

With the change in scenery comes a change in dating dynamic. From fireworks at ALTITUDE to exotic staycation spirits at Sirén, poolside oral ice hockey at Float, singles umbrella tag, and cabana-hopping across Gaslamp rooftops, there is much flirting to pursue and fun to have this summer.

Discover flirty tips for summer fun on San Diego rooftops.

Set the mood by pulling your date over to the edge of ALTITUDE Sky Lounge to watch the Sea World fireworks display if she’s the romantic type, or if she’s more of a sports buff, catch the final innings of the Padres game! 

Elevator Joy-Riding: It can be tough to get away from the crowds! But if you’re clever, the rooftop bars provide you with ample opportunity for some “covert missions.” Grab your date, sneak into one of the elevators (Stingaree has a good one) and ride it up and down while you have a private make-out session. 

Count Constellations: A fun conversation-starting game that’ll work in your favor. Wage a bet with your hot prospect at Firehouse or Ivy Rooftop to see who can find and name the most constellations in 5 minutes. Loser ponies up their phone number…or a kiss. 

A rooftop bar like Sirén is a prime place to play "Stranger Pick-up" if you’re a couple. Set the scene by ordering a Mai Tai and pretend you’re in an exotic location like Tahiti. Then as you sip your drink, have your man play a stranger and proceed skillfully seduce and “pick you up,” staying in character as you let him seduce you and frolic around the bar as if you had just met. Draw out the vacation fling as long as you want! 

If you’re hanging out at one of the pool parties, like Hard Rock’s Intervention, on a hot summer day, challenge your date to a little “Ice Hockey” by putting an ice cube in your mouth and seeing how long you can push it back and forth between your mouths before it melts! (pictured)

Play the Tourist Game. Okay, Okay, I hope I don’t get reprimanded for this but there’s just something about those rooftop bars that put you in vacation mode! As long as your intent is harmless, start chatting up the guy or gal you’ve got your eye on and play the part of a tourist who’s come to San Diego for the first time. Maybe you need “showing around.” Throw out an Aussie accent and ask where the best spots are to go, and they’ll be on you like white on rice. 

Play the “Fantasy Vacation” Game. Okay if you’ve got the guts to pull off the game above, include the person you’re chatting up in fun game and propose that you pretend that you’re somewhere else besides San Diego for the next hour. Agree upon the fun fantasy spot, then order some Blue Hawaii’s and get caught up in the excitement as you both fill in the details of where you are, what you’re doing; extra points for trying to speak their native tongue. The silliness of the game creates massive bonding! Just be careful you don't get caught by security ...

Cabana Hopping Fugitives. If you can’t afford to rent out your own cabana, grab your date and play cabana “hop till you get caught,” ducking into each cabana and seeing how long it’ll take for you to get discovered.…Then, hop into another one and repeat! 

Umbrella Tag. With your group of friends, grab a little drink umbrella and assign a dating ‘dare’ to it. For example, whoever gets the umbrella “Must kiss whomever I’m talking to on the cheek,” or “Must ask whomever I’m talking to for their number.” Then pass the umbrella off to a different one of your friends every 5 minutes and watch the fun go down. 

Rooftop Rule of Thumb: Keep it classy, San Diegans! When the outdoors, sun, alcohol, and bodies of water are involved, class and etiquette tend to get…a little sloppy. Relax and enjoy yourself but mind your P’s and Q’s and keep your swimwear on, hold your liquor in the sun, keep the body shots to a minimum, don’t untie peoples’ swimsuits on “accident” (I’m talking to you, men!), and bring a change of clothes; you don’t want to be the girl walking around the clubbers at Hard Rock in your itsy bikini and straw hat. 

Pictured: Love-struck local at KIN Lounge, the terrace bar at Manchester Grand Hyatt. Check out more San Diego nightlife photos at all your favorite rooftop lounges, and discover more elevated nightlife ideas at the Top Ten Rooftop Lounges in San Diego.

If you’re looking for summer love, check out DeAnna Lorraine’s new line-up of HOT singles events and Lock & Key parties for young professionals, every 1st and 3rd Friday of the month beginning June 19 at the hottest nightclubs downtown. Visit her site for details on her singles events and new Date Coaching packages.