The Art of Mindful Dating in the Digital Age

Ken Page, a psychotherapist and the author of Deeper Dating: How to Drop the Games of Seduction and Discover the Power of Intimacy, has devoted his career to helping people fall in love—the deep, committed, mutual kind of love that lasts a lifetime. And he has come to a blunt realization: “We’re victims of terrible information. We’re told that the great secret to finding love is making yourself more desirable, more attractive. But, in reality, that’s painful and self sabotaging because you’re focusing on what’s not good enough about yourself and that leads you to date from a place of profound insecurity.”

A far better alternative, Ken says, is making the search for love a mindful undertaking, one that begins with self-acceptance and moves forward with openness and authenticity. “When you change the way you behave on dates and learn to lead with your true self, your luck changes. Love is what happens when you share your deepest gifts with bravery and generosity.” Here’s how to apply the principles of mindfulness to the search for love:

Set Your Intention

Write a brief mission statement on why this journey matters to you, says Ken. A mission statement might include statements like, “I want a life of shared adventures” or “I want a sense of family in the world.”

Juliet Kaska was in her mid-30s with a highly successful career as a Los Angeles Pilates instructor when she decided to take a dating sabbatical. She had had an active but unsatisfying romantic life with, she says, “a smorgasbord of men.” Through sessions with a therapist and daily meditation, Juliet explored whether she wanted to get married and what she was looking for in a husband.

Juliet realized she wanted a mate who had, she says, “a successful life.” That meant, yes, an established career, but also hobbies, interests, friendships, a family life. Out went her on-again-off-again relationships with men who were fun but had no interest in settling down. Several months later, Juliet dove back into the dating world.

It felt different this time. “Because I knew what I wanted; I wasn’t going into dates worried that what he wanted was someone younger or skinnier. The insecurity was lifted and that made dating light and fun and interesting.”

In December 2013, Juliet met Simon, a movie producer who is originally from South Africa. “With Simon there was a connection that was otherworldly, and he was the kindest human being I’d ever met. I knew.” In June 2017, Juliet and Simon married in the coastal city of Durban, South Africa. “I’d gotten that internal voice that says you’re not good enough, you can’t get what you want, you don’t deserve it to finally pipe down,” Juliet says.

When you’re ready to get started on your own love quest, Ken suggests this micro-meditation. Take two or three minutes to evoke a few of the people who have loved you the most. “They may be alive or not,” he says, “but they are still close to your heart and they would want the best for you, including a relationship that brings you happiness.” Visualize their faces as you imagine them offering words of encouragement. “Let their support infuse you,” Ken says.

Stay in the Present

When you’re eager for a committed relationship, it’s easy to become so focused on conjecture about a possible future with the person you’re dating that you undermine the chances of achieving a genuine connection.

“That’s when your date turns into a job interview,” says Judith Sills, Ph.D., a psychologist and the author of A Fine Romance: The Passage of Courtship from Meeting to Marriage. “Instead of trying to interrogate a prospective partner, let yourself experience him or her the way you experience your friends. You’re really just trying to have a lovely conversation where you can exchange ideas in an easy, relaxed way. It’s not about, ‘Should I rule you out as a lifetime companion?’”

Forget, “What happened with your last marriage?” or “How many serious relationships have you had?” or “Where do you see yourself in five years?” Instead, opt for neutral, open-ended questions about, say, a recent vacation, a new running regimen or favorite local restaurants. These are questions that convey, “I’m interested in getting to know you. I’m not gathering information about your social status.”

Staying in the present also means tolerating ambiguity, which is one of the challenges in the early stages of a romance, says psychologist Michelle Skeen, Psy.D., the author of Love Me, Don’t Leave Me: Overcoming Fear of Abandonment & Building Lasting, Loving Relationships.

“You can’t know where a relationship is going on the first or fifth date,” she says. “You might not even know whether he or she is dating other people, and that lack of certainty can be very uncomfortable.”

To handle the uncertainty, try to relax into the present moment as much as you can. After all, says Michelle, projecting into the future can lead you to overlook vital information that’s right in front of you, such as whether the other person shares your values.

Amy Bastianelli, a 31-year-old clinical social worker in Kennett Square, Pennsylvania, remembers a feeling of unease when she was dating her first husband. “I totally checklisted him,” she says, “from ‘Will he be a good provider?’ down to ‘Likes dogs.’ I’d read these studies that couples are most likely to be successful if they come from similar religious and socioeconomic backgrounds. That was true for us, and I wasn’t able to see beyond that to what was really important. Or, rather, I ignored my gut feeling that we weren’t aligned, that our relationship was completely and utterly devoid of any emotional or spiritual connection.”

Try your best to put aside the spreadsheets and the crystal ball so you can tune into the vibe between you and the person with whom you’re sharing a cocktail, dinner or a hike. Pay attention to your feelings, Ken says. Do you feel pleasure? Warmth? Is there a sense of fun? Do you feel inspired? Unsafe? Criticized? Do you like who you are in the presence of this person? Does he or she bring out your best self?

Be Your True, Vulnerable Self

Many of us are striving to provide “perfectly sculpted responses” as we text, message or get together with new dates, Ken says. “But there’s got to be this feeling of essential comfort, and you won’t get to that if you’re trying to be polished and perfect.”

That’s what Amy believed when she decided to try dating through the new MeetMindful app after her marriage collapsed. “I was determined to not filter myself, to not think about what I should and shouldn’t say,” she says. On her profile, she wrote that she was a single mom looking for intimacy, friendship and a deep spiritual connection.

The night before her first date with Eric McKinley, a Philadelphia public defender, she texted him that she was nervous because she hadn’t been on a date in the nine years since she’d met her ex-husband. “That’s something I never would have shared with my ex,” Amy says.

In fact, her first date with her ex-husband had been an uneasy one. “I remember thinking, ‘Should I order salad or a steak? What would each say about me?’ It was this ‘other-izing’ of myself, trying to see myself as he would see me.”

With Eric, there was none of that. From the beginning, “I was not at all self-conscious,” she says. “I was completely comfortable around him.” The proof: on their first date, Amy ordered crab nachos and a beer. “That was what I wanted and I didn’t care what impression I made or how messy the nachos would be.”

In late October, 10 months after they met, Amy and Eric wed in New Orleans before a small group of friends and family.

“It keeps getting better,” she says of their relationship. Still, staying true to herself requires vigilance. “To this day, I will sometimes relapse. I need to be mindful of not trying to be who I think Eric wants me to be.”

Take, for example, when he asks, “Do you want the charred Brussels sprouts?” and she says yes. “He’ll look at me and say, ‘Really? What’s going on with you?’ And he’s right. I don’t want the Brussels sprouts,” Amy laughs. “It’s a reminder that Eric fell in love with the real crab-nacho me, and that’s who I’m going to be.”

Finally, Ken offers this tip: “When you’re feeling enthusiastic about someone, let yourself show it,” he says. “Once you make the choice that you’re only going to date people with whom you can be yourself, you protect yourself from jerks, you speed up the process and you give yourself permission to take pleasure in savoring the rich moments of connection.”