"I'm 28. An 18-Year-Old Wanted to Go on a Date With Me. I Said No. Am I Weird?" episode artwork

EPISODE · Mar 14, 2026 · 28 MIN

"I'm 28. An 18-Year-Old Wanted to Go on a Date With Me. I Said No. Am I Weird?"

from You Don’t Know Anything About Women: Dating Stories and Advice · host Roy Calvin | Dating Advice

Here's who I'm giving REAL dating advice for men to in this episode:- A guy with no prospects and no sex in the past 7 years who quickly cut things off with a girl after one date.- A guy whose photo got posted on Facebook by a girl he was dating because she wanted dirt on him.- An ugly, boring guy with no personality wondering how he could ever attract a woman (me and him actually aren't so different). - A guy living in a huge city (Phoenix) but still can't find any women to date.- A guy who has so many women in his life that he rejected an 18-year-old who wanted to go on a date.Subscribe for more Reddit dating stories, dating advice for men, and dating tips.Message me or support the show: https://linktr.ee/roycalvinDating lessons from this epiosde:Do not cut things off after one date because of a texting argument. Texting can create misunderstandings, especially when personal topics come up too early. If the woman was good in person and you do not have other options, it is usually better to meet again before throwing the situation away.Texting should mainly be used to make plans, not to argue about personal issues. Long emotional conversations over text can damage a dating situation before it has a chance to develop. Save serious topics for in-person conversations and use texting mostly to set up the next date.If you regret ending things with a woman, send the message and get your answer. Worrying about seeming needy is less important than finding out whether there is still a chance. If you want to see her again, be straightforward, accept the outcome, and avoid sitting in regret.Women-only Facebook dating groups are creepy and invasive when they post about men before a date. Being posted in a private group with your name, location, and dating details can feel like a privacy violation. If a woman posts about you before even meeting, it is reasonable to feel creeped out and cancel the date.“If you have nothing to hide, you have nothing to worry about” is a bad dating privacy argument. Being a decent guy does not mean strangers should be able to discuss your personal life in private groups. Men should not have to give up privacy because other men behave badly.Do not rely on women randomly showing interest in you if you want a dating life. Most men will not have women approaching them, complimenting them, or openly flirting with them. If you want results, you need to pursue women directly instead of waiting to be chosen.If you think you are ugly or boring, you still need real data from approaching women. Feeling unattractive does not prove that women will reject you. You need to actually approach women, ask for numbers, and create a large enough sample size before deciding what is or is not working.Dating apps are not enough for most men, especially if the top of the funnel is weak. If online dating gives you few matches or no dates, you need to create opportunities in real life. Cold approach, malls, Target, parks, and other public places can work if you actively talk to women instead of waiting for perfect openings.Ditch the business card when cold approaching women. Handing a woman your business card can make the interaction feel like networking instead of dating. If you meet a woman in public, talk to her normally, get her phone number, and follow up like a man who wants a date.Do not reject an attractive 18-year-old just because of an age gap if she is legally an adult. If she wants to go on a date and she is attractive, do not decide for her that the age difference is wrong or that you have nothing in common. Go on the date first, then decide based on the actual interaction.

Here's who I'm giving REAL dating advice for men to in this episode:- A guy with no prospects and no sex in the past 7 years who quickly cut things off with a girl after one date.- A guy whose photo got posted on Facebook by a girl he was dating because she wanted dirt on him.- An ugly, boring guy with no personality wondering how he could ever attract a woman (me and him actually aren't so different). - A guy living in a huge city (Phoenix) but still can't find any women to date.- A guy who has so many women in his life that he rejected an 18-year-old who wanted to go on a date.Subscribe for more Reddit dating stories, dating advice for men, and dating tips.Message me or support the show: https://linktr.ee/roycalvinDating lessons from this epiosde:Do not cut things off after one date because of a texting argument. Texting can create misunderstandings, especially when personal topics come up too early. If the woman was good in person and you do not have other options, it is usually better to meet again before throwing the situation away.Texting should mainly be used to make plans, not to argue about personal issues. Long emotional conversations over text can damage a dating situation before it has a chance to develop. Save serious topics for in-person conversations and use texting mostly to set up the next date.If you regret ending things with a woman, send the message and get your answer. Worrying about seeming needy is less important than finding out whether there is still a chance. If you want to see her again, be straightforward, accept the outcome, and avoid sitting in regret.Women-only Facebook dating groups are creepy and invasive when they post about men before a date. Being posted in a private group with your name, location, and dating details can feel like a privacy violation. If a woman posts about you before even meeting, it is reasonable to feel creeped out and cancel the date.“If you have nothing to hide, you have nothing to worry about” is a bad dating privacy argument. Being a decent guy does not mean strangers should be able to discuss your personal life in private groups. Men should not have to give up privacy because other men behave badly.Do not rely on women randomly showing interest in you if you want a dating life. Most men will not have women approaching them, complimenting them, or openly flirting with them. If you want results, you need to pursue women directly instead of waiting to be chosen.If you think you are ugly or boring, you still need real data from approaching women. Feeling unattractive does not prove that women will reject you. You need to actually approach women, ask for numbers, and create a large enough sample size before deciding what is or is not working.Dating apps are not enough for most men, especially if the top of the funnel is weak. If online dating gives you few matches or no dates, you need to create opportunities in real life. Cold approach, malls, Target, parks, and other public places can work if you actively talk to women instead of waiting for perfect openings.Ditch the business card when cold approaching women. Handing a woman your business card can make the interaction feel like networking instead of dating. If you meet a woman in public, talk to her normally, get her phone number, and follow up like a man who wants a date.Do not reject an attractive 18-year-old just because of an age gap if she is legally an adult. If she wants to go on a date and she is attractive, do not decide for her that the age difference is wrong or that you have nothing in common. Go on the date first, then decide based on the actual interaction.

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"I'm 28. An 18-Year-Old Wanted to Go on a Date With Me. I Said No. Am I Weird?"

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This episode is 28 minutes long.

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This episode was published on March 14, 2026.

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Here's who I'm giving REAL dating advice for men to in this episode:- A guy with no prospects and no sex in the past 7 years who quickly cut things off with a girl after one date.- A guy whose photo got posted on Facebook by a girl he was dating...

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