Since my divorce I've spent over $10,000 dating online, and I'm still single — I don't even know a woman right now who's interested in me that way. And yet it's been worth every dollar, because the real return wasn't a relationship. It was getting to know myself, having fun, and getting clear on exactly what I want.
Yes, I put it on credit cards
I'll be honest about the part people find crazy: I borrowed all of it. It went on credit cards, and I'm paying it down on a fixed plan with a balance transfer. Most people would tell me to stop — quit dating, quit spending, get the money right first. I understand the instinct. I just don't agree with it, because I think the right relationship is an investment, not an expense.
The right partner pays for itself
I'm looking for a second wife and at least two more kids — a healthy woman who wants a family and supports the work I do. Here's why that's financial as much as romantic: when I'm with the right woman, I produce. Fifteen years ago my ex-wife inspired me to start on YouTube in the first place. The right partner who's proud of what I build, who watches and even makes videos with me, more than pays for the cost of finding her.
A date that relaunched my channels
The clearest proof came right after I'd deleted all my YouTube channels and was completely burned out. I went on a date with a woman from Talkify who's a full-time content creator, and just talking with her about what she was doing lit a fire under me. That same day I started four brand-new channels from scratch. In under three months they've pulled more than 300,000 organic views combined. I'm good at this — the analytics, the clipping, using AI to assemble it — and she reminded me of that. One date did that.
What $10k taught me about what I want
Going out with a wide range of women — and learning where my limits are — got me clear fast. I don't want to hook up. I don't want polyamory. I want one woman I love like crazy, marriage, kids, a happy home, and a thriving business built alongside her. I'll be friendly with everyone, but I won't waste my time: you've either got that with me or I'm not interested. I even had a date where I wasn't attracted and caught myself over-disclosing and signaling red flags on purpose — which taught me something about myself too. Without paying for those dates, it would have taken me far longer to figure any of this out.
From paid apps to free cold approach
Here's the ironic ending. After dropping money on premium features and even $200 on Hinge roses, all that paid practice gave me the confidence to do the thing my mind least wanted to do — cold approach, which is completely free. So now I start conversations with women everywhere I go, and I'm about ready to head down to the pier and just see what happens. The money bought the self-knowledge; the self-knowledge made the free version possible.
Your dating is worth investing in — that's the whole lesson, and it's the same theme as why dating a lot doesn't mean you're desperate. If this resonates, you can watch my dating playlist here.