Ways to Prepare for a First Date and Where to Go

Cassie Zampa-Kiem (photo courtesy of Innovative Match)

New year, new you, new relationship? Finding a valentine or playing the field in 2022 doesn’t have to be as painful as getting shot with Cupid’s arrow. Marin’s own dating and relationship strategist Cassie Zampa-Keim, founder and CEO of Innovative Match, has been matchmaking for more than three decades. She shares her expert advice on how to prepare to captivate your date and make the meeting go as smooth as Richardson Bay waters on a calm day. 

The Setup

“The most important thing is to make a date feel easy,” says Zampa-Keim. “Atmosphere goes a long way when it comes to picking dating spots.” She suggests those who want to meet for a coffee date choose somewhere cozy. For a dinner date, opt for an intimate and casual but sophisticated destination that isn’t one of your go-to spots. Make it special! It’s a romantic rendezvous, not a business meeting or a lunch break. 

Steer away from scheduling a longer outing for a first date — generally plan for 45 minutes to an hour, max. While out, separate yourself from technology and refrain from checking your cellphone. 

The Glow Up

“It’s very important to make a physical and mental change before a date,” says Zampa-Keim. “You need to switch from day mode to date mode, even if your date is during the day.”

Brighten up your lipstick shade, try out some shiny new shoes, let your hair down, remove the stuffy tie. Go back through any messages you might have exchanged with your date to take note of the small details that person might have shared. 

“If you do your homework before the date by brushing up on your information about them, you will feel more at ease,” says Zampa-Keim. “People are also often concerned that their date won’t find them attractive or that they won’t find their date attractive. Just keep an open mind and your expectations in check.” 

Show Up

Once you’ve sat down and settled in, Zampa-Keim recommends finding some topics of interest to talk about. Be conversational and open-minded. Avoid anything you wouldn’t normally consider light and breezy for a first encounter with anyone. And remember every person is unique and has their own interests that make him or her special. 

“Do you both like to work out? Travel? Go to art museums? Those topics are all fair game,” she says. “You can talk about your kids, but in moderation. You’re on a date, not them. As for talking about your ex, past relationships, politics and sex? Don’t. And don’t speak negatively while on a first date, ever — you will only come off as angry and unpleasant. But remember to be conversational, and take time to listen.”


If you feel like the meeting went well, Zampa-Keim has some tips for turning one date into a second (or third). “Too many times there are missed signals,” she says. “If you enjoyed your date, but they didn’t say anything at the end about seeing you again and you would like to see them, send a quick text the following day saying that you had a nice time. You will be able to gauge by the response if your relationship will be moving forward.”

And remember to be open-minded about the future of the relationship. “I learn from every person I meet and I tell my clients to look at dating the same way,” she says. “Not everyone is looking for a spouse — some people are seeking a long-term relationship, a companion, an activity partner, a romance or some combination.”

The Happily Ever After 

Fueled by her passion for making matches and providing guidance paired with a genuine admiration for the resilience of the human spirit, Zampa-Keim says love is and has always been at the top of her list of priorities. 

“Prioritizing what I want for myself is always at the top of my list, no matter how many lists I made. If it was love, it still is. I want to give that gift to others.”

Five Fabulous Places for a First Date

Red Whale Coffee Bar 

169 Paul Drive, San Rafael

This is a cozy spot to meet a date. It feels tucked away and offers a sense of safety and seclusion to meet someone new for the first time. Whether you’re here for a caffeine boost or you are truly focused on meeting the one, it’s known as a judgment-free zone. 

Left Bank Brasserie 

507 Magnolia Avenue, Larkspur 

Stepping into Left Bank feels like you’ve traveled to eternally romantic France. It’s named after the “Rive Gauche” in Paris — and can be just as romantic on a first date. A spot that once served as a popular destination for San Franciscans to dance and picnic under the stars is now a beautiful place for meeting someone new. 


234 Magnolia Avenue, Larkspur 

Perry’s on Magnolia offers a casual atmosphere and welcoming service. Opt to dine outside beneath the dazzling display of twinkling lights strung between the canopy of giant redwood trees for a little added romance. 

Buckeye Roadhouse 

15 Shoreline Highway, Mill Valley 

This historic Mill Valley eatery is a favorite for visitors and locals alike. Its cozy, intimate Aspen lodge–like dining room is complete with a fireplace and true old-world charm. Enjoy traditional American cuisine in a classic setting made for good conversation. 


2233 Larkspur Landing Circle, Larkspur

Farmshop Marin is nestled into the heart of Marin Country Mart. Dine with style here in the airy dining room, on the expansive outdoor patio, or at the full-bar area and lounge. Farmshop is great for dinner, drinks or brunch in a relaxed but elevated setting.