I recently watched a woman post a video about how lonely she is — and in the same breath insist on how happy she is being single. Everything else told the opposite story: her expression, her other videos, the way she described sitting home alone on Friday and Saturday nights, up until two or three in the morning watching Carl Jung lectures and telling herself other people just don't think deeply enough for her. Then came the conclusion: "I just like being single. Nobody bothers me, and I get to live my adult life." It doesn't add up, and I think a lot of single people are running the same script.
Step one is honesty
The first thing to do is be honest with yourself: you're miserable being single. That kind of honesty isn't a problem — it's the opening, because once you admit it, you know what to do about it. The trap is self-deception. When you go around insisting "I'm so happy being lonely," you bury the very thing you'd have to face to change it.
I can say this from both sides. I've had about a decade single and 15 years in a relationship, and I'm single again now. I'm genuinely enjoying this season — I have a ton of friends, men and women, young and old, and my kids stay with me several nights a week. But I'm under no illusion that single is better. When I got divorced, the biggest loss by far was the depth of that relationship, and I was very aware of being unhappy by comparison.
Relationships are wealth
Here's the frame that makes it click for me: the highest level you'll ever reach in life is always with other people. Relationships are wealth, and a great partner is a massive form of it. Yes, there are small perks to being single — I get to keep only the healthy food I want in the house instead of the ultra-processed stuff someone else might buy — but I'd move the right woman in tomorrow, because I know how much happier a great relationship is. If you've never had a decade with someone where you were never lonely, you may not even know what you're missing.
This is different from staying in something dysfunctional. If a relationship is hurtful and mean, being single absolutely beats it. But a healthy relationship isn't what you're comparing against when you tell yourself you're fine alone.
"I love being single" is like "I love being broke"
Put it in money terms and the self-deception gets obvious. Imagine someone saying, "I love being broke. I can't afford anything, and I get to complain and feel like a victim." You'd know instantly they don't love it — they just haven't put in the work to have money. Having money is great. Security is great. Dating is the same: it's the equivalent of having a job you genuinely love. Friends and family matter enormously, but in this analogy they're the side hustles, the investments, the inheritance. A loving partnership is the foundational, number-one way you bring real relationship wealth — love, joy, and connection — into your life.
Do the work
So get honest, and then go to work. I've spent more than $10,000 on dating in the last six months and I go out consistently — I've got dates lined up this week. One of these connections is going to turn into marriage, more kids, and building an awesome life together, and that is so much better than being single that it's hard to even describe waking up next to a partner you love and getting to do life together. Is dating hard? Of course. A woman I matched with on a dating app told me the same thing this week, and she's right. But hard isn't a reason to quit — building a business I love was hard too, and it was worth every bit of it. The work is worth doing. I went deeper on how my own approach to all this has changed in I can't date like I did 15 years ago, and you can find more in my dating videos here.