Ken Page, LCSW, is a psychotherapist, the author of Deeper Dating, host of the Deeper Dating Podcast, and a member of WeDeepen's faculty. Christina Weber calls him one of her mentors in love: "I go to him all the time when I need relationship advice." In episode 106 of her podcast, he named the two patterns he sees derail people looking for love most often, and what to do about each. This guide sums up that conversation. Quotes are from the episode transcript, lightly edited for readability.
Discouragement fatigue
Ken once asked everyone on his email list where they get most stuck in dating. More than a hundred people answered, and he sent each a personal voice message back. One woman named the problem in two words: discouragement fatigue.
It's the slow wear of trying again and again. Dating relationships that don't work. Long-term relationships that end in heartbreak. What Ken calls "the culture of unkindness" in so much of the dating world, the swipe apps, and the disappointment of doing it all over again. It hits hardest after what he calls stepping-stone relationships: you've done the inner work, you meet someone who seems different, and it ends the same way, only worse, "because their hopes were higher."
His answer isn't to try harder. It's to change what you measure. "The degree to which you uplevel the way you search for love is really the degree to which you're going to uplevel the kind of person you're going to meet." In place of "Did this one work out?", he offers three questions:
- Am I becoming more self-treasuring?
- Am I becoming more vulnerable?
- Am I becoming more discriminating?
"If the answers to those questions are yes, you are on the right path." That, he says, is how you find light in the middle of the tunnel, not just at the end of it.
The wave of distancing
The second pattern is the one Ken calls "the worst saboteur of healthy new love that exists." If you're used to people who are not quite available, then the moment you meet someone who is truly present, your attraction can suddenly drop. "All of a sudden you notice their nose hair. You notice that their laugh irritates you. You notice that your sexual desire diminishes." In his experience, between a third and a half of all people who date go through it, and "nobody's taught to deal with it."
His guidance: expect it, and don't let it make the decision for you. He borrows a line from Marianne Williamson: "both feet in until both feet out." With someone truly available, he says, "you will be afraid, you will be nervous, you'll want to escape," but "it passes if you let the love deepen and it's the right person."
The one question to date by
Attraction matters, Ken says, but it shouldn't come first. His central question: "Does my soul feel safe with this person? Frame your entire search for love around that question and watch what changes." When your soul feels safe with someone who is present, available, and mutually attracted, "that's the happiness you could glide on almost forever."
He's also direct about two things that stall progress no matter how much inner work you've done: active addiction, and serious psychiatric conditions that haven't been stabilized. Get help with those first, he says, or "you're going to tread the same ground again and again."
Your scariest ask is your core gift
Christina shared a story from her own love life. Ken had urged her to ask a partner a question she was afraid to ask. She resisted all evening, then asked. Whatever the answer, the relief was immediate, and the relationship got more honest.
Ken's reading of that moment is the heart of his Deeper Dating approach, which centers on naming and honoring your core gifts: "The things we're most afraid to share and most afraid to ask for not only are often the most important things, they are our deepest core gifts." And: "The parts of ourselves we leave behind in order to get love or approval are the parts of ourselves we need to champion and reclaim in order to really find healthy love."
Christina put the flip side plainly: "The true feeling of abandonment, I've found, is when I abandon myself."
How this fits WeDeepen's approach
Ken's work lines up closely with WeDeepen's premise that love is a trainable skill. The Four Pillars say the same thing in different words: growth comes first, with no attachment to outcome; you own your own experience; and all feelings are welcome, including the fear that shows up when someone good arrives. Both Ken and Christina stress support: nobody gets better at love alone. That's why WeDeepen runs a weekly live session and community and Love Immersion retreats in Austin. To practice with others, join the membership. Come play with us.
FAQ
Who is Ken Page?
Ken Page, LCSW, is a psychotherapist, the author of Deeper Dating, host of the Deeper Dating Podcast, and a member of WeDeepen's faculty.
What is discouragement fatigue?
It's the exhaustion that builds from repeated dating disappointments, breakups, and unkindness, a term one of Ken Page's readers coined. He suggests measuring progress by whether you're becoming more self-treasuring, vulnerable, and discriminating, not by whether each relationship lasts.
What is the wave of distancing?
Ken Page's term for losing attraction or wanting to escape just as you meet someone truly available. He estimates it affects between a third and a half of people who date, and says it usually passes if you stay present and the person is right for you.
What question does Ken Page recommend asking when dating?
"Does my soul feel safe with this person?" He suggests framing your whole search for love around it, alongside attraction.
Where can I listen to the full episode?
Episode 106 is on the WeDeepen podcast page, Apple Podcasts, and YouTube.