10 Oct 2026
"I Let Girls Choose $1,000 First Dates...Can I Just Take Them on Walks Instead?"
Here's who I'm giving REAL dating advice for men to in this episode:
- A guy wondering if confidence is needed or not to have success in dating (he's worried about "emotional availability").
- An overthinker who is wondering if a woman's willingness to meet on a weeknight means she's not interested.
- A guy asking if it's okay to invite girls out on walking dates (the comments are atrocious).
- A frustrated guy who had no luck at his first speed dating event.
- A married guy who's been with his wife for 22 years, has only ever slept with her, and says his sex life sucks.
Subscribe for more Reddit dating stories, dating advice for men, and dating tips.
Message me or support the show: https://linktr.ee/roycalvin (https://linktr.ee/roycalvin)
Dating questions answered this episode:
Is confidence really that important in dating? Yes. Confidence isn't a magic fix, but it makes every part of dating easier, especially handling rejection. A confident guy who gets turned down thinks "okay, onto the next one," while a guy without it spirals into believing he'll be single forever. Women rarely name confidence as what they like; they just describe you as fun to be around.
Do you need to build confidence before you start dating? No. Confidence is not a prerequisite for dating. It's a loop: success with women builds confidence, and confidence brings more success. You just have to insert yourself into that loop somewhere, and the fastest way is to go out and start talking to women instead of reading about it or watching videos first.
Is "fake it till you make it" confidence dishonest?
No. Acting more confident than you feel is how most men get the early experience that builds real confidence. Women can sense how you carry yourself, and waiting until you feel fully confident before acting just means waiting forever. There's nothing disingenuous about pushing yourself past your comfort zone.
How can you tell if a woman's interest has dropped? If she's still agreeing to meet you, her interest level doesn't really matter. Asking whether it dropped is overanalyzing. Women who lose interest early usually just end things, so a woman who says she can't do a weekend but can do an evening is still telling you yes. Take the date.
Are walking dates a good first date idea? They can work, but a walk alone isn't ideal because you can't see her face while you talk. A better move is inviting her for something cheap like coffee or a smoothie and adding a short walk before you sit down. You don't need to be tall or good-looking to pull off a low-cost date, just confident in your plan.
Should you let a woman choose where to go on a first date? No. Always plan the date yourself. Women generally prefer a man who can make a plan, and letting her pick opens the door to her choosing an expensive restaurant. If a woman only agrees to meet because of a fancy dinner, the restaurant is the reason she's there, not you.
How much should you spend on a first date? Very little. A first date doesn't need to cost more than a coffee or a $7 smoothie, and there's a wide range of options between a free walk and a thousand-dollar dinner. Splitting the bill is fine too. Spending big to impress her puts her on a pedestal and attracts the wrong kind of woman.
Why did I get no matches at a speed dating event? Usually it's your conversation, not your looks. Being tall and well dressed only gets you to baseline. If this was your first event, getting zero matches is normal and not a verdict on you. Treat it as practice, sharpen how you talk to women, and go to another one.
What should you talk about with a woman on a first date? Skip the topics every other guy uses, like her job, where she lives, or how many siblings she has. Those make you forgettable. Say the slightly surprising...
