38 MONTEREY COUNTY WEEKLY MAY 15-21, 2025 www.montereycountynow.com FACE TO FACE The story is a familiar one. A person graduates from high school, marries, has children and eventually divorces. Within that script, however, Alisal High School graduate Cheryl Sharp started a real estate agency—Steinbeck Real Estate, with offices in Salinas and Toro Park— before retiring after almost 40 years. At the same time, Sharp realized the pitfalls of dating at an older age, especially with two children. Although naturally shy, she had gained confidence in approaching and communicating with people through her work with clients. So Sharp began offering dating coach services, as well. The Monterey resident began work on a book, cataloging the techniques she learned to improve confidence in social settings. But, as Sharp points out, “life happened”—a businesswoman of the year award, a 2011 federal tax evasion charge, getting married again, and all the while growing the business and managing a staff of 75. “Post Covid I thought, ‘I should pick this up again,’” says Sharp. “I have so much material.” Last year she began coaching in earnest, offering workshops for both women and men, focusing on singles 40 and over. Her book, Back in the Game: Navigating the Dating and Social Scene, is in the final editing stage before publication. Weekly: Dating coach? I don’t think it’s a college major. Sharp: There’s no dating coach PhD [laughs]. It’s life experiences. I was basically pretty shy. I had to figure out a strategy. When I went on a date, I was a freaking nervous wreck. I had to learn these mind games for myself—“go talk to him. I’m too afraid to talk to him.” You’d be surprised how many people don’t know how to talk to strangers. It’s good to tell a child not to talk to strangers, but you’re 50 or 60. You can talk to a stranger: “Here’s my card, here’s my number. You seem interesting, call me sometime.” All you’re doing is planting a seed. It’s about being mindful and open and purposeful. Are there other things that hold people back? People have judgments: “There is nobody here.” “I’m too old.” “What would my kids think?” I try to abolish those judgments. My generation, people met in high school or college, were married for 30 or 40 or 50 years, had kids, lived in a bubble of maybe six friends. And now you’re going to start dating again? Your base of knowledge is from college. That’s where I come in. When I covered nightlife in Dallas, women told me they looked at a guy’s shoes and teeth. My mother said shoes, teeth and haircut. There’s male profiling and female profiling. If a woman says, “I always pick the wrong guy,” it’s because usually Miss High Maintenance won’t be interested in Mr. Shy and Lonely Guy in the corner. It’s about finding out what you are looking for. You have to be mindful and aware. Is there a common complaint you hear? There are no single men in Monterey. I hear it from the men, too: there are no single women here. Go to where people are. Go to car shows, go to food and wine events. Engage in conversation. I was at an event at the Yacht Club. My friend said, “There are no men in Monterey.” There was one right behind her. Cindy is still dating that guy. What about dating apps? Dating apps—no. If you’re out, you can make real-life connections. Dating apps, you have zero chance—zero—of learning about that person. I could preach all day. You were in real estate. When you retired you started this. Do you take time off? I was always a runner. I’m an advanced scuba diver—I’ve dived all over the world. I’m not just a workaholic. I know I have to carve out time for myself. You know, one of the things I would do every Tuesday, I’d leave the office at 4 and hike Soberanes. I’ve hiked all over Monterey County. When I start to feel stress, I go outside. Which is your favorite activity? Scuba. Oh my god, when you are underwater everything is slow. There’s an ebb and flow—the seaweed, the schools of fish. I was in Bali and a huge pod of maybe 20 manta rays went by. It was just beautiful. It is so peaceful. Any final dating tips? Like sending someone a drink? Send over a drink. It might turn into a conversation, it might not. It’s just being friendly. When you’re out, compliment people. Get used to smiling and making eye contact. Every technique is empowering. Date Saved After retiring from real estate, Cheryl Sharp returned to a role she learned along the way: dating coach. By Dave Faries “Watching their transformation, whether it’s building self-worth, taking risks, or setting higher standards, is the most fulfilling part of what I do,” says Cheryl Sharp, defining success as a dating coach. DANIEL DREIFUSS Noodle Want to meet Noodle? Please ll out our online adoption questionnaire. If you’d like sponsor our next ad, give us a call. 831-718-9122 | www.POMDR.org Noodle may look a little scru y, but her gentle spirit shines through. With patience and love, she’s ready to bloom into a devoted companion. This tenderhearted pup thrives in a quiet, reassuring home where she can feel safe, loved, and nally understood. Maltese, Female, 6 y/o, 15 lbs Ad sponsored by M.B.W.W.C. www.GoWhales.com Visit Our New Bene t Shop! Monday - Saturday 10:00 am - 5:00 pm Come see the hidden gems, upscale goods, and nd your new favorites! 223 Grand Ave, Suite 1 Paci c Grove 831-718-9122 | www.POMDR.org BENEFIT SHOP
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