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If You've Just Met...
Toast with a tasting flight
When you’re meeting a blind date, a little liquid courage goes a long way. Try a tasting flight at taprooms like Modern Times, Stone Brewing, Mike Hess, or Ballast Point, whose Little Italy taproom lets you try four 4-ounce tasters for $8—just enough sips to let your gut decide whether you want to stay a while longer or say buh-bye.
Go on a not-your-average stroll
Forget the typical paths—pick a more dynamic walk like the San Diego Botanic Garden in Encinitas ($18 per adult or free for members), where you can alternate conversation about your jobs and pet peeves with a look at more than 4,000 species of plants. For something more energetic, hit up a farmers’ market—Imperial Beach’s holds court by the ocean on Fridays—or a street festival like Adams Avenue Unplugged, Normal Heights’ weekend music and food fest held every April.
Make dinner more adventurous
Beat those awkward pauses at Wrench & Rodent Seabasstropub’s omakase dinner in Oceanside, offered nightly. The term means you let the chef pick the dishes (tell your server your budget in advance so they can determine the number of dishes, or just tell them when you’re full). Make sure to book a seat at the sushi bar so whenever those first-date silences creep in, you can just focus on chef slash owner slash mad scientist Davin Waite as he crafts sashimi, passion-fruit-flavored soups, and vegan options. For something a little farther south, Hidden Fish also offers omakase.
Break the ice at Belmont Park
Take your first date to Nostalgia Town with some carnival fare, games, and primo people-watching at Belmont Park, San Diego’s 94-year-old amusement park in Mission Bay. Riding the Giant Dipper is a must; the historic wooden roller coaster tops out at 48 miles per hour for a one-minute adrenaline rush. And while it’s no longer 15 cents to ride, as it was when the park opened (now $6), the butterflies in your stomach are the same. (Then again, maybe that’s a sign of a second date!)
Jet-set for the day to another city
High rollers can kick-start a relationship on a private plane. Carlsbad’s Schubach Aviation coordinates customizable one-day round trips from McClellan-Palomar Airport. Charter a jet for a day of preplanned activities, like a rare vintage wine tasting and cave dinner in Napa (starts at $14,000 for a couple). Another operator out of that airport, Latitude 33 Aviation, can also tailor experiences with a concierge and will offer discounted one-way flights when they’re returning from a one-way elsewhere. A private charter can set you back at least $7,500, but your date will gush about it all the way down the aisle.
If You've Been Together 1 Year...
Make it "Instagram official" at The Flower Fields
Your family and close friends may know you’re dating, but now it’s time to declare it to the masses, and you’ll need an impressive backdrop to do it. The Flower Fields’ Giant Tecolote Ranunculus begin to bloom at this Carlsbad landmark next month (through Mother’s Day). Walk to the top of the hill to get a full scope of the flower beds. They also host special events, like their Field to Vase dinner (below) on April 18.
Indulge at Petco Park
The Padres are celebrating their 50th this year—only 49 years ahead of you and your partner. At Petco Park, get tri-tip nachos from Seaside Market or pizza, wine, and even a fresh-cut flower from Buona Forchetta, then whoop it up in your seats to get on the video board.
Sail into the sunset
Feeling pressure to take things to the next level or answer "Where is this relationship going?" Lighten things up by renting a FunCat—a miniature, electric-powered catamaran with lounge chairs—for up to a four-hour cruise in Mission Bay when you leave from Paradise Point Resort & Spa. After you’ve docked, head to the resort’s Barefoot Bar & Grill to say cheers to another year.
Get competitive at trivia night
Does your partner have a temper? Are they a sore loser? You’ll find out during an innocent game of questions about music, movies, history, and esoteric political factoids. Some of our favorite spots include Shakespeare Pub in Mission Hills (Sundays), Del Mar’s Viewpoint Brewing Co. (Mondays), The SandBox in Pacific Beach (Thursdays), and Gossip Grill’s Smarty Pants Saturday Brunch in Hillcrest.
Do a winery crawl
See, swirl, sniff, sip, swish, and savor your way through San Diego’s urban wineries in Little Italy—consider Carruth Cellars’ romantic patio or Pali Wine Co.’s quaint rooftop—hit the road toward Temecula for a day, or head below the border to Valle de Guadalupe. One year in, it’s the perfect setting to ask your partner to finally meet your parents. Wine not?
Picnic in style
You’ve wooed your partner at all the nice eateries around town. It’s time to personalize your dining with a sunset picnic. Bring your blanket and unpack your basket at Mount Helix Park, Sunset Cliffs Natural Park, or your favorite beach. Or pay to take the setup and cleanup off your plate with Pop Up Picnic Co., which brings the goods to you in select areas in San Diego County (Sunset Cliffs included). Order just the grub—like charcuterie boards or a rotating seasonal menu—or add a little ambience with tables, chairs, pillows, and blankets.
If You've Been Together 5 Years...
Park it at the drive-in
Congrats! You’ve graduated from the timeline of being high school sweethearts, but that doesn’t mean you have to act like an old married couple just yet. Tuck into one of San Diego’s drive-in movie theaters—Santee Drive-In Theatre or South Bay Drive-In Theatre—any day of the week for a double feature (and no remorse about not telling Mom and Dad why you’re not home by curfew).
Stargaze in the mountains
Just over an hour from San Diego, perched 4,800 feet up Palomar Mountain, is the Observatory Campground ($15–$30 per night). Cement pads are handy to set up telescopes, and if you’re camping, you’ll have grills, fire rings, picnic tables, and in peak season, flush toilets and coin-operated showers. Then visit nearby Palomar Observatory to see the Hale Telescope, which famously analyzed the Andromeda Galaxy.
Horse around on a ranch
A half decade in, your quarrels have meant you’ve both fallen from the horse and decided to get back on many a time. Make the metaphor literal with horseback riding at The Ranch at Bandy Canyon in Escondido. Most rides cost $75 for an hour, but there’s also the optional upgrade to a specialized trail ride package, which can be customized for occasions like birthdays, anniversaries, or—dare we say—marriage proposals.
Upgrade your farm-to-table dinner
Farm-to-table is good, but eating on the farm right where the ingredients are grown is better. Oceanside’s Cyclops Farms hosts a Quarterly Water Bill Dinner ($100 per person), with a portion of the proceeds going toward paying their utilities and other upkeep. The night starts with a tour of the 2.5-acre farm, before big-name local chefs Samantha Parker (Privateer Marketplace & Wine Bar) and Daniel Pundik (Local Tap House) cook with ingredients plucked just a few feet away from your seat.
Party for a cause
Nothing strengthens a relationship like showing compassion for others—so why not do it with some style? Put on a tie for Art Alive (April 11–14 at the Museum of Art) and the Chefs, Cork & Craft Gala (April 27 at San Diego Food Bank’s warehouse). Go casual for Feeding San Diego’s Pairings with a Purpose (April 13), and get in costume for The New Children’s Museum’s annual fundraiser (November 9 at the museum), which is always fun and playful—last year’s theme was "A Totally 80s Birthday Bash," with a Tom Cruise impersonator and Cheers-themed bar.
If You've Been Together 10 Years...
Splurge on an over-the-top couple’s spa treatment
By now you’ve learned silence can be golden. Visit a luxury spa, close your eyes, and treat yourselves right. The "Lovers’ Ritual" at The Spa at Rancho Valencia begins with a scented bathtub soak; next, you paint each other with oils and mineral clay, take in a sun bake, rinse, enjoy side-by-side massages, and finish with a fruit plate and Champagne. The "Ultimate Escape" at Park Hyatt Aviara’s Aviara Spa involves four hours of alone time with your SO—two scrubs, two massages, two facials, an organic lunch, and one uninterrupted hour in the couple’s suite, which is outfitted with a fireplace, outdoor heated Whirlpool, and indoor Swiss shower for two. Ooh là là.
Listen to dueling pianos
Give your vinyl records or Spotify playlist a break in favor of a little live music—and competition—at a dueling piano bar, like The Shout! House downtown, where two performers post up at face-to-face grand pianos to play rock ’n’ roll hits from the ’50s to the present. Word to the wise: It gets a little rowdy on the weekends. For a mellower, noncompetitive alternative, head to the historic Red Fox Steakhouse and Piano Bar in North Park, closing in March but rumored to be reopening soon nearby.
Become cocktail connoisseurs
Time to put that bar cart from your wedding registry to real use. Sign up for a cocktail class at You & Yours Distilling Co. for the basics on shaking, stirring, and pouring tipples like real hosts do. The hourlong session ($45 per person) is held the first and third Wednesday of every month at 6:30 p.m. using their housemade gins and vodkas, and comes with two cocktails per person to enjoy and bottles available to purchase.
Take a lesser-known hike
After a decade, you’ve been there and done that obligatory photo at Potato Chip Rock, Torrey Pines, and Sunset Cliffs. Take a hike around the lesser-traveled trails, like Los Peñasquitos Canyon Preserve or, for a challenge, Cuyamaca Peak, where you can pitch a tent for the night.
Train it to downtown LA for a day
The worst part about LA is driving. Thankfully, when you hop on the Pacific Surfliner from downtown’s Santa Fe Depot, Solana Beach, or Oceanside, you can get to DTLA in under two and a half hours—no road rage required. Once you’re there, take a ride-share to lunch at Grand Central Market, a giant food hall serving everything from New York–style bagels to noodle bowls and pastries; check out The Broad museum, whose walls are lined with Warhols, Lichtensteins, and the reservation-required Infinity Mirror Rooms by acclaimed Japanese contemporary artist Yayoi Kusama; shop the Arts District (ROW DTLA has multiple boutiques in one space); and have an early dinner at the buzzy Middle Eastern spot Bavel before training it home.
If You've Been Together 20 Years...
Take an ultra-luxe staycation
The Lodge at Torrey Pines’ Putt & Pamper Package (from $1,819) gets you a two-night stay, two rounds on the Torrey Pines Golf Course, and two spa treatments. L’Auberge Del Mar’s "From the Sea With Love" package (from $7,500; through March 31) includes one night in their Del Mar Suite, a Rolls-Royce ride to a bubbly and caviar picnic, massages, a wine-paired aphrodisiac-inclined dishes, and a rose petal turn-down.
Appreciate art after hours
Leave the kids at home and enjoy the peace and quiet of the San Diego Museum of Art, which stays open until 8 p.m. on Fridays. On display this month are sculptures by Javier Marín and installations by Tim Shaw. On the way out, head to the Sculpture Court for cocktails, craft beer, and live music, (usually jazz and soul) at the alfresco gastropub Panama 66.
See a big-name chef in action
The new Fort Oak in Mission Hills, from the team behind Hillcrest’s Trust restaurant, has a 16-seat table that wraps around the kitchen, where you’ll interact with Executive Chef Brad Wise and his team. At Little Italy’s Kettner Exchange, exec chef Brian Redzikowski hosts monthly five-course menus for up to 12 people at a table in the kitchen. The February 20 theme is "Chinese New Year 2019: Year of the Pig," with a pork-centric, Asian-inspired menu.
Go bowling at a hip alley
If you haven’t been bowling since your kid chose it for a birthday party, the new crop of alleys are less musty, more must-Instagram. Punch Bowl Social in the East Village spans eight lanes, two bocce courts, shuffleboard, an arcade, and gourmet takes on diner fare spearheaded by Top Chef alum Hugh Acheson, plus old-school cocktails like Negronis. In San Marcos, Bowlero boasts 40 black-lit lanes, HD screens playing family flicks, and even beer pong tables.
Snuggle up for outdoor theater
Reconnect with your partner in a blanket under the stars. The Moonlight Amphitheatre’s summer 2019 season brings The Producers, Matilda, West Side Story, and Victor/Victoria. We recommend getting reserved lawn seating (they provide lawn chairs) and bringing a picnic when the gates open 90 minutes before curtain. Can’t wait until summer? Catch live entertainment at Club M, the indoor "venue" with pub and dinner seating on the actual Moonlight stage. Their winter lineup features Kiss and Tell: Valentine’s Cabaret (February 1), Spencer Day: The Look of Love (February 16), and David Burnham: Mostly Broadway (March 2).
If You've Been Together Forever...
Go mezcal tasting
Swap out your beer, wine, and martini diets for a taste of the hottest spirit in town—mezcal. Tahona in Old Town boasts a tasting room with over 100 variations of the agave-based liquor and a bar manager able to tell a story about each of them. Book a sit-down tasting (starting at four pours for $25) any day of the week or drop in for live guitar music on Sundays, and yes, they host Taco Tuesday, too.
Dress up for charity
If you’ve grown too comfy around each other in sweatpants, it’s time to dress up for a cause. Our favorite black-tie galas include: Rady Children’s Charity Ball (February 9 at Hotel del Coronado), The San Diego Opera Lover’s Ball (February 23 at The US Grant), and Rendezvous in the Zoo (June 15) to enjoy the San Diego Zoo sans grandkids.
Try coffee cupping
Did you know you can sip, analyze, and contemplate coffee just like wine? At Café Virtuoso in Barrio Logan, settle into an hourlong class ($15 per person) alongside their Q Grader (like a sommelier) to learn how to "grade" coffee. Little Italy’s Frost Me Gourmet hosts free sessions that include three to five roasts. Both cafés offer cupping classes by request.
Put a modern spin on a movie theater date
Relive first-date movie theater memories at Cinema Under the Stars, Mission Hills’ year-round outdoor movie theater. They play new movies and classics like Breakfast at Tiffany’s on a 20-foot screen with HD projection, surround sound, and a variety of seats (single and double zero-gravity reclining, love seats, and deck chairs with ottomans). Concessions are also cheaper than typical theater snacks, with coffee, candy, and microwave popcorn at $2 each. For another option, Rooftop Cinema Club at the Manchester Grand Hyatt is rumored to be back in April.
Have a laugh together
Give yourselves a break from hearing each other’s jokes a hundredth time over and attend a comedy show at one of San Diego’s humor houses, such as Comedy Heights in University Heights, American Comedy Co. downtown, or The Comedy Store in La Jolla, all of which draw performers from both San Diego and around the US.
Dance like no one’s watching
Studies show that dancing improves brain health, so start moving and encourage your partner to do the same. Learn salsa, bachata, African, and other styles at North Park’s A Time to Dance. For lessons combined with food and drink, there’s InCahoots, the country line-dancing bar in Mission Valley. If you’re 55 or older, San Diego’s Parks and Recreation Department hosts themed Senior Dances ($5, 619-236-6905) every second and fourth Thursday of the month at the Balboa Park Club. Just want to sit and feel the rhythm? Pampas Argentine Grill in Serra Mesa showcases live tango every Friday and Saturday night, while downtown’s Café Sevilla has flamenco dinner shows on Friday and Saturday nights (and classes Tuesday through Thursday).