"I Want to Play Tennis With One Girl and Date Another...This is Cheating, Right!?" episode artwork

EPISODE · Feb 28, 2026 · 30 MIN

"I Want to Play Tennis With One Girl and Date Another...This is Cheating, Right!?"

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 who was taking it "slow" with a girl (AKA they weren't even dating) and now she hooked up with someone.- A guy who knows that he needs to approach women, but freeze up when he tries.- A guy who desperately wants to forget about a girl that he loves (HE broke up with HER so wtf?) + a story about a girl who was banging me while her boyfriend wasn't in the country.- A worried guy wondering if his girlfriend who moved 4 hours away should be instantly replying to his texts (and my advice for when girls you hang out with go travel somewhere).- A guy who feels guilty just because he hangs out with more than one women throughout his week.- An ugly-duckling (self-proclaimed) who is suddenly getting TONS of female attention (what happened?).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:If your crush sleeps with another guy, forget about her and pursue other women. Even if you thought she liked you, sleeping with another guy shows she is not acting like a woman who is seriously interested. Do not pedestalize her, do not wait around, and do not chase one girl when you should be pursuing several.Taking it slow with a woman can make you lose the opportunity. If you like a woman, you need to act on your intentions instead of slowly hoping something develops. Going too slow out of “respect” can leave you hurt when she chooses a man who moves faster.How to start a conversation with a girl: give yourself permission to fail. Most men do not approach women at all, so taking action already puts you ahead. You may freeze, stumble, or say something awkward at first, but practicing cold approach is how you build confidence.Cold approach gets easier when you stop judging success by the phone number. The first win is making yourself approach, not whether she gives you her number. Some days will be bad, some days will be good, and failure is temporary if you keep talking to women.The best way to get someone out of your head is to meet more girls. If you are stuck replaying a woman in your mind, dating and sleeping with new women is the most effective way to detach. Even temporary distraction with another girl is better than sitting alone in mental replay.Do not always end things just because a woman is thinking about another man. If she is still seeing you, sleeping with you, and not actively dating someone else, it may be better to keep the situation going instead of cutting it off too quickly. Take advantage of what is in front of you while it lasts.If a woman moves away temporarily, keep expectations low and stay lightly in touch. A woman being four hours away for an internship does not have to end the connection, but you should not get needy about slow replies. Check in occasionally, consider visiting, and accept that the situation may fade.Slow texting does not automatically mean a woman is losing interest. If she still apologizes, replies, and has shown affection in person, do not assume every delayed message is rejection. Texting every day may be unnecessary, especially when the better move is to set up the next time you see her.You can date multiple women at once when nothing is official. After one date, you do not owe exclusivity to anyone. You can keep meeting new women, keep seeing the girl you have chemistry with, and even play tennis with another woman if there is no official relationship.If women suddenly show interest in you, stop self-sabotaging and escalate. Getting more attention means you need to practice turning interest into dates, kissing, sex, and real experience. You may feel inexperienced, but you deserve the opportunity, and the only way to get better is to go for it.

Here's who I'm giving REAL dating advice for men to in this episode:- A guy who was taking it "slow" with a girl (AKA they weren't even dating) and now she hooked up with someone.- A guy who knows that he needs to approach women, but freeze up when he tries.- A guy who desperately wants to forget about a girl that he loves (HE broke up with HER so wtf?) + a story about a girl who was banging me while her boyfriend wasn't in the country.- A worried guy wondering if his girlfriend who moved 4 hours away should be instantly replying to his texts (and my advice for when girls you hang out with go travel somewhere).- A guy who feels guilty just because he hangs out with more than one women throughout his week.- An ugly-duckling (self-proclaimed) who is suddenly getting TONS of female attention (what happened?).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:If your crush sleeps with another guy, forget about her and pursue other women. Even if you thought she liked you, sleeping with another guy shows she is not acting like a woman who is seriously interested. Do not pedestalize her, do not wait around, and do not chase one girl when you should be pursuing several.Taking it slow with a woman can make you lose the opportunity. If you like a woman, you need to act on your intentions instead of slowly hoping something develops. Going too slow out of “respect” can leave you hurt when she chooses a man who moves faster.How to start a conversation with a girl: give yourself permission to fail. Most men do not approach women at all, so taking action already puts you ahead. You may freeze, stumble, or say something awkward at first, but practicing cold approach is how you build confidence.Cold approach gets easier when you stop judging success by the phone number. The first win is making yourself approach, not whether she gives you her number. Some days will be bad, some days will be good, and failure is temporary if you keep talking to women.The best way to get someone out of your head is to meet more girls. If you are stuck replaying a woman in your mind, dating and sleeping with new women is the most effective way to detach. Even temporary distraction with another girl is better than sitting alone in mental replay.Do not always end things just because a woman is thinking about another man. If she is still seeing you, sleeping with you, and not actively dating someone else, it may be better to keep the situation going instead of cutting it off too quickly. Take advantage of what is in front of you while it lasts.If a woman moves away temporarily, keep expectations low and stay lightly in touch. A woman being four hours away for an internship does not have to end the connection, but you should not get needy about slow replies. Check in occasionally, consider visiting, and accept that the situation may fade.Slow texting does not automatically mean a woman is losing interest. If she still apologizes, replies, and has shown affection in person, do not assume every delayed message is rejection. Texting every day may be unnecessary, especially when the better move is to set up the next time you see her.You can date multiple women at once when nothing is official. After one date, you do not owe exclusivity to anyone. You can keep meeting new women, keep seeing the girl you have chemistry with, and even play tennis with another woman if there is no official relationship.If women suddenly show interest in you, stop self-sabotaging and escalate. Getting more attention means you need to practice turning interest into dates, kissing, sex, and real experience. You may...

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"I Want to Play Tennis With One Girl and Date Another...This is Cheating, Right!?"

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This episode is 30 minutes long.

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This episode was published on February 28, 2026.

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Here's who I'm giving REAL dating advice for men to in this episode:- A guy who was taking it "slow" with a girl (AKA they weren't even dating) and now she hooked up with someone.- A guy who knows that he needs to approach women, but freeze up when...

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