You Don’t Know Anything About Women: Dating Stories and Advice

Roy Calvin | Dating Advice
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There's a lot of clueless guys asking for dating advice on Reddit, and there's just as many people providing them with terrible guidance. If I replied to their posts with the advice they actually need, I'd just get banned and be told that I'm an idiot by the other commenters (despite having been on more dates with more women than all of them combined). That's where this podcast comes in. I'm checking out the most cringeworthy, clueless dating and relationship posts from Reddit to provide REAL dating advice for men that the gatekeepers of the internet don't want you to know.

  1. 6d ago

    "A Girl Who Rejected Me 8 Years Ago is Now Divorced With 2 Kids and Finally Wants to Date Me!"

    Here's who I'm giving REAL dating advice for men to in this episode: - A 26-year-old who started dating 8 months ago and has gotten his heart rekt already (the girl told him she wanted to take things slow). - A guy who had a girl with a long-distance boyfriend flirting with him HARD, but he blew it. - A guy who has been contacted by a girl that rejected him before she had 2 kids and is now looking for a life raft. - A guy who recently started cold approaching and is worried about being seen by people he knows (the comments had it all wrong). - A 36-year-old, bald, short guy who has had absolutely no success in dating. Subscribe for more Reddit dating stories, dating advice for men, and dating tips. Message me or support the show: https://linktr.ee/roycalvin Dating questions answered this episode: Why did she lose romantic interest after three months of dating? Waiting until the fifth date to kiss and failing to create opportunities for intimacy may have contributed to the loss of attraction. The advice is to escalate earlier, try for a kiss on the first or second date, and create practical opportunities to spend time alone together.How often should you see someone when you are newly dating? Eight dates over three months is not necessarily too slow. Dating once or twice a week is not a requirement, and a pace of roughly eight dates in three months can be perfectly reasonable when both people are busy.What should you do if you live with your parents and have nowhere private for a date? You still need to figure out the logistics of spending time alone. That could mean using a separate living space, planning an activity that naturally leads somewhere private, or arranging another practical solution rather than repeatedly going on dates with no path toward intimacy.What should you do if a female friend acts romantic but says you are just friends? Do not keep asking her to define the relationship. Her words should be taken seriously, but if you are interested, make your intentions clear through your actions and ask her to spend time with you one-on-one rather than trying to get verbal confirmation of what the relationship means.How can you tell if a woman is flirting or just naturally affectionate? Look at how she behaves around other men before assuming that physical affection means romantic interest. Someone who is naturally touchy with many friends may behave intimately without intending to flirt, so the surrounding context matters.Should you stay friends with a woman you actually want to date? If you are attracted to her, pretending you only want friendship can keep you stuck in a situation that is not what you actually want. Make a move, accept the possibility of rejection, and then decide whether continuing the friendship makes sense.Should you date a woman who rejected you years ago and now wants a relationship? Past rejection alone does not have to determine the decision, because people and circumstances change. In this case, however, the major issue is that she now has two children, which the advice treats as a reason to walk away rather than overlooking the situation simply because she is interested now.Is it normal for a man to go out alone to meet women? Yes. Going out specifically to meet women is presented as a deliberate dating strategy rather than something embarrassing. If meeting women is not happening naturally through your hobbies or daily routine, you may need to intentionally create opportunities to talk to them.Does “just do your hobbies and you will meet women” actually work? Not necessarily. If spending years playing video games, going to the gym, or doing hobbies has not resulted in meeting women, continuing to wait for dating opportunities to appear naturally may not change anything. The alternative presented is to deliberately talk to single women through approaches, dating apps, or actual dating events.What should you do if years of dating rejection have destroyed your confidence? Stop assuming that more of the same approach will eventually produce different results. The advice is that years of rejection can understandably make someone negative, but the solution is to change the dating strategy and create more opportunities to actually talk to single women rather than relying on female friends, social events, or expensive dating coaches.

  2. Aug 1

    "I Smell Like Garbage and Plan to Live on $15K a Year...Why Can't a Find a Girlfriend!?"

    Here's who I'm giving REAL dating advice for men to in this episode: - A guy who is worrying about offending girls when he talks to them after he approaches other girls. - A guy accusing girls of "giving up" on the relationship when he hasn't even asked them out. - A former video game addict who now cares about his appearance and healthy hobbies because of a girl. - An extremely frugal guy who makes a living dumpster diving but can't find a girl who wants to be part of that (he's a serial Reddit complainer). - A guy who played it safe...and the girl he was dating ghosted him (a tale as old as time). Subscribe for more Reddit dating stories, dating advice for men, and dating tips. Message me or support the show: https://linktr.ee/roycalvin Dating lessons from this episode: Approaching women after rejection is not as embarrassing as it feels. Most people are not watching your every move at a bar, on the street, or in public. If one woman turns you down, you can still talk to another woman instead of assuming everyone noticed.Do not worry about making a woman feel like a second choice. If she did not see the first rejection, it does not matter, and if she did see it, she can still choose whether she wants to talk to you. Approaching gives you a chance; doing nothing gives you zero.If the energy feels stale after a few rejections, change locations. You do not need to quit for the night, but moving to a different bar, street, or area can reset your mood. Sometimes a fresh environment helps you keep approaching without carrying the weight of the last rejection.Dating app conversations should not drag on for weeks before a real invitation. If you are texting every day and building momentum, ask her out by day two or three. Waiting too long gives the connection time to fade before anything real happens.A vague “we should go out sometime” is not a real date invitation. Give her a specific plan or at least specific days you are free. If you leave the timing up to her, you are making her lead, and most women will not do that for you.Nothing from a dating app matters until you meet in person. Long texts, jokes, and apparent chemistry can vanish overnight. Until she actually comes out with you, the connection is not real enough to treat like a relationship.A crush can motivate self-improvement, but do not let one girl become the whole reason. If liking a woman pushes you to dress better, create art, play music, or improve your life, use that momentum. Just make sure the new habits become yours, not something you only do hoping she notices.Do not decide a woman’s answer for her before you ask her out. If you still want to give it a shot, send the message and invite her properly. Assuming her silence means no may be correct, but you only know for sure if you actually ask.If your lifestyle makes dating nearly impossible, you may need to change the lifestyle. Extreme frugality, low income, no car, and plans to live on very little money will shrink your dating pool. If you want a wife, kids, or a normal family life, your money and lifestyle need to match that goal.Playing it safe on dates can kill romantic momentum. If you only hug after two strong dates, avoid physical escalation, and never invite her home, you may come across too passive. Women can say they want to take things slow, but you still need to lead, escalate, and create progression.

  3. Jul 18

    "I Sent Her Nudes and She Sent Me Fakes...I Can Still Trust Her, Right?"

    Here's who I'm giving REAL dating advice for men to in this episode: - A guy who talks to girls on apps but never asks them out and wonders why they lose interest. - A guy who thinks his uncle goes and picks up random girls in his cool car at will. - An immigrant in a brand new country who doesn't know how to meet girls (they're all around him). - A guy who feels like he gets too anxious unless he's dating multiple women (this is a GOOD thing). - A clueless guy who sent nudes to a girl on a dating site but really it was probably a guy in Nigeria. Subscribe for more Reddit dating stories, dating advice for men, and dating tips. Message me or support the show: https://linktr.ee/roycalvin Dating lessons from this episode: Dating app conversations should turn into dates quickly. If you talk to women online for weeks or months without asking them out, you are creating the reason they lose interest. Ask for the date within a couple of days instead of trying to build a fake relationship through messages.Do not wait for women to ask you out. If you are the man, you need to move things forward. A woman may match with you, text you, and seem interested, but that does not mean she will be the one to suggest meeting.Stop swiping on women you are not willing to meet. If a woman lives two or three hours away and you know you will not make the trip, do not waste time matching with her. Dating apps only matter when they lead to real-life dates.Nothing on a dating app is real until you meet in person. Texting can feel like progress, but it is not a relationship, and it is barely even real dating. Until you meet face-to-face, you should treat the conversation as temporary and fragile.If you know a man who is good with women, ask him how he does it. Do not sit around feeling jealous of someone who seems to pick up women easily. If your uncle, friend, or someone close to you has success with girls, use that access and learn from him.Dating as an immigrant is easier when you approach women directly. You do not need a friend circle before you start dating. Street approach, malls, grocery stores, and everyday public places can help you meet women and learn the city at the same time.Do not rely on Meetup groups or friend circles to create your dating life. Hobbies, events, and friendship groups can be useful for life, but they are not a consistent dating strategy. If you want women, go meet women directly.Dating multiple women can help reduce anxious attachment. If one woman is your only option, you are more likely to overthink texts, get clingy, and panic when she pulls away. Having multiple options keeps you calmer and helps you choose better.You do not need to tell women about every other woman you are dating. Until exclusivity is clearly established, you can date multiple women without giving a full report. Most women do not actually want to know every detail about who else you are seeing.Do not send sexual photos to strangers from dating sites. If someone online asks for nude photos before you have met, assume something is wrong. It may be a scam, a fake profile, or someone trying to use the photo against you.

  4. Jul 4

    "I Asked for Permission To Touch Her Chest, She Said Yes, Then She Freaked Out!"

    Here's who I'm giving REAL dating advice for men to in this episode: - A guy who had a trip booked with his parents before he met his girlfriend, and she says he needs to cancel. - A guy who keeps getting interrupted by his girlfriend trying to show him Instagram garbage when he just wants to relax and play video games. - A guy wondering if he got scammed when the girl he was on a date with suddenly invited a friend (some commenters thinks he missed out on a threesome). - A guy who feels like he has to constantly be searching for girls. - An autistic guy who asked for permission to touch a girl's "chest" while they were in his car. Subscribe for more Reddit dating stories, dating advice for men, and dating tips. Message me or support the show: https://linktr.ee/roycalvin Dating lessons from this episode: Relationship boundaries matter more than keeping your girlfriend happy every second. If your girlfriend wants you to cancel a family vacation that was planned before the relationship got serious, you should not rearrange your life around her anxiety. A strong relationship should be able to survive a short trip.Separation anxiety in relationships is not always your problem to fix. If a woman detaches after only three or four days apart, that is something she needs to manage. You can be understanding, but you should not spend your life trying to prevent her from feeling alone.Texting while on vacation should not become emotional babysitting. You can message your girlfriend while you travel, but do not turn the trip into a full-time job of reassuring her. Go enjoy the vacation and deal with relationship problems when you get back.How often you see your girlfriend sets the tone for the whole relationship. If you train a woman to expect constant access to you, time apart will feel like a crisis. Keep enough independence early on so a week or two away does not become a major relationship problem.Alone time in a relationship needs to be clearly protected. If your girlfriend keeps interrupting you while you are gaming, working, or relaxing, tell her calmly that you need uninterrupted time. Do it outside the heat of the moment so it does not become a fight.A girlfriend who interrupts you constantly needs a clear boundary, not endless patience. Tell her when you are about to be busy, ask if she needs anything first, and then expect her to wait. She can send videos, photos, or reels for later instead of demanding your attention every minute.Bringing a friend on a date is a first-date red flag. If a girl invites a friend 20 minutes into the date or says she needs emotional support, leave. A date is supposed to be one-on-one, not a setup where you entertain her friend too.Who pays on a date should not include paying for her friend. If a woman brings another girl and expects you to cover both of them, do not play along. Paying for extra drinks or meals will not make her like you more, and it can turn you into the night’s free tab.Dating anxiety can be useful if it pushes you to take action. Feeling pressure to meet women is not automatically bad. Use that energy to approach, date, and create options instead of sitting around watching dating videos and hoping confidence appears.Physical escalation on a date should happen in steps. Do not jump straight to sexual touching, and do not make every move a stiff verbal permission request. Start with smaller touches, read her reaction, go for the kiss, and let the interaction build naturally.

  5. Jun 20

    "She F'd Her Co-Worker While I Was Dating Her and Another Girl. How Could She Do This!?"

    Here's who I'm giving REAL dating advice for men to in this episode: - A guy who is worried that he's going to be able to see the girl he's dating "only" 3 times in the next 6 weeks. - A virgin who can't believe that two people would ever want to have a one night stand (it's not as simple as he thinks). - A guy whose pride is keeping him from going on a second date (I tell a story about a time when I made the same mistake). - A self-sabotager who doesn't want to meet a girl again because he thinks he can't improve her life. - A hypocrite who can't believe the girl he was dating (now his girlfriend) hooked up with her co-worker just a few weeks after meeting, even though he did the same thing with her (he was also juggling multiple women). Subscribe for more Reddit dating stories, dating advice for men, and dating tips. Message me or support the show: https://linktr.ee/roycalvin Dating lessons from this episode: Do not overthink dating momentum after a great first date. If the first date went well and the next date is already planned, you do not need to panic about losing momentum. Early dating works best when you stay interested without becoming overly eager.Two weeks between dates is not too long in the early stages of dating. A busy schedule does not automatically mean low interest. Seeing someone every few weeks can still build attraction, especially when the connection is strong and both people have real-life obligations.Texting after a first date should be light, confident, and purposeful. You do not need to text all day or force constant communication. A couple of thoughtful messages between dates can keep the connection alive without putting pressure on the situation.Video calls are usually unnecessary in early dating. If you are only waiting a week or two for the next date, you do not need to rely on video calls to maintain attraction. In-person chemistry matters more than trying to build a relationship over the phone.Casual dating and one-night stands are often less planned than people think. Many one-night stands happen because one person later decides not to continue, not because both people clearly agreed in advance that the encounter would be casual and temporary.Someone who rejected you once is not always treating you like a backup option. People can change their minds for many reasons, including timing, mood, uncertainty, or personal circumstances. Rejecting someone purely out of pride can cause you to miss a real dating opportunity.Do not let pride ruin a second chance in dating. If someone reaches back out and you are still interested, it may be worth setting up another date instead of assuming the worst. Staying calm and direct is often better than acting from resentment.Do not decide you are not good enough for someone you like. If a woman agrees to go on a date with you, let her decide whether she enjoys your company. Self-rejection, anxiety, and insecurity can sabotage a connection before it has a chance to grow.Most women will not initiate the second date, even if they are interested. Waiting for her to ask you out again is not a reliable way to measure attraction. If you want a second date, take the lead and make a clear plan.Exclusivity in dating doesn't need to be clearly discussed early on. If two people have not clearly agreed to be exclusive, conflict can happen when one person dates or sleeps with someone else. Clear expectations matter more than vague assumptions about loyalty.

  6. Jun 6

    "My Girlfriend Says She's Too Insecure to Do Arts & Crafts Together...Should I Finally Dump Her?"

    Here's who I'm giving REAL dating advice for men to in this episode: - An autistic guy who wants to apologize to the girl he's dating over and over when he makes mistakes. - A university student who asked a girl out, got a NO, and is wondering how to deal with still regularly seeing her (it's time to be cool). - A guy who is worried about competing against other guys and offending girls. - A serially friendzoned guy who thinks girls like him. - A guy who has been complaining about his insufferable girlfriend online for over a year but still hasn't broken up with her. (Also, I somehow managed to say the F word literally 50 times in this episode. More than twice a minute. Enjoy that.) Subscribe for more Reddit dating stories, dating advice for men, and dating tips. Message me or support the show: https://linktr.ee/roycalvin Dating lessons from this episode: Over-apologizing in a relationship can create more pressure than the original mistake. If you already apologized and your girlfriend has moved on, bringing up the same small mistake again can make the situation feel worse. A sincere apology is usually enough.Relationship anxiety can lead to rumination, reassurance-seeking, and self-sabotage. When you replay small mistakes for days or weeks, the real issue may be anxiety rather than the mistake itself. Constantly asking for reassurance can put unnecessary strain on the relationship.Learning how to stop apologizing repeatedly is important for relationship confidence. After you apologize once, the best move is often to stay calm, stop revisiting the issue, and return to normal behavior. Repeated apologies can make you seem less secure.Rejection feels worse when you have limited dating experience. Being rejected by someone you like can feel devastating, especially if you spent months building up your feelings. The key is to accept the answer, stay composed, and keep meeting new women.Seeing someone after they rejected you does not have to be awkward. If you share classes, hobbies, or mutual friends with someone who turned you down, the situation is only as awkward as you make it. Be polite, relaxed, and avoid acting bitter.Do not build your hobbies around impressing a girl. Sports, fitness, and hobbies should be things you enjoy for yourself. If your motivation depends on one woman’s approval, rejection can make you lose interest in something that could still benefit you.Dating success is a numbers game, and a few rejections do not define your attractiveness. A small number of failed attempts does not mean you are undesirable. One yes can change your entire outlook, so focus on increasing your opportunities instead of obsessing over a temporary losing streak.Sliding into DMs is not the only way to meet women. If Instagram, dating apps, or online messaging feel too competitive, meeting women in real life can help you stand out. A real conversation gives you more context than a random message.Unwanted attention often depends on whether attraction is mutual. You cannot always know in advance whether a woman will welcome your attention. Make a respectful move, accept rejection if it happens, and do not assume every approach is automatically unwanted.Staying in an unhappy relationship in your early twenties can waste valuable dating years. If a relationship is emotionally draining, one-sided, or full of repeated complaints, it may be better to end it than keep hoping things will change. Your early twenties are an important time to gain dating experience and learn what you actually want.

  7. May 23

    "She Has Kids From 2 Other Men and Demands the 'Princess Treatment,' So I Pay For Everything!"

    Here's who I'm giving REAL dating advice for men to in this episode: - A guy who doesn't want to have sex with his new girl because he's starting a new job in a month (even though he hasn't gotten laid in a year). - A 25-year-old guy who thinks that the guys getting girls are "complete trash." - An insanely jealous guy who is worried that his older girlfriend with kids is gonna find someone else (they just started dating and are already having huge fights). - A guy who is paying for everything for his girlfriend (she demands a "princess treatment") who has two kids from two different men. - A guy who let a girl slip through his fingers all because he didn't want to meet one hour later than originally planned. Subscribe for more Reddit dating stories, dating advice for men, and dating tips. Message me or support the show: https://linktr.ee/roycalvin Dating lessons from this episode: Do not self-sabotage when a woman clearly wants to have sex with you. If you like her, find her attractive, and she is willing, turning down the opportunity for vague or overly cautious reasons can ruin the momentum. Men should take advantage of good dating opportunities when they appear.Dating a coworker is risky, but the situation changes if you are already leaving the job. It is usually smart not to date where you work, but if the connection has already started and you are leaving soon, the risk may be less serious than it feels in the moment.Do not put words in a woman’s mouth and then react as if she said them directly. In the first post, the man claimed the woman called him a “p***y,” but he was the one who introduced that word. Men should avoid escalating a situation based on their own framing.Self-improvement alone will not fix your dating life. Going to the gym, earning money, eating clean, and having your life together are useful, but they will not automatically make women appear. Men still have to actively talk to women and create opportunities.Dating apps often do not work well for average men, so real-life approaching can be more effective. If dating apps are giving you few matches, no replies, or no dates, cold approaching women in real life may be more effective than relying only on apps.Cold approach is a numbers game, and a few rejections mean almost nothing. Approaching only a few women is not enough to judge whether cold approach works. Increase your number of approaches before deciding that women are not interested.Asking for exclusivity too early can make you look anxious and desperate. Men should not beg for exclusivity or repeatedly ask whether a woman might meet someone else. Stay calm, avoid needy conversations, and accept that a woman could always choose someone new.Major arguments early in dating are a serious warning sign. If a relationship is already filled with conflict, emotional repair, and pressure to prove yourself, it may not be worth saving. Early dating should not feel like constant damage control.Do not pay for constant “princess treatment” without reciprocity. Paying for dates, flowers, gifts, beauty expenses, and emotional support while receiving little in return creates a one-sided relationship. Set the tone from the beginning and avoid becoming a provider for someone who does not appreciate it.When a woman gives you a chance to meet, make the date happen. If she asks to move the date by one hour and you want to see her, be reasonable and make it work. Losing a date over a small scheduling issue can cause the connection to fade before it starts.

  8. May 9

    "I Hired A Dating Therapist, But She Gave Up After 5 Sessions Because I'm Hopeless!"

    Here's who I'm giving REAL dating advice for men to in this episode: - A guy who says he can easily talk to girls...but is too scared to actually start the conversation. - An autistic guy who was seeing a dating therapist (she wanted him to lie to girls) but she cut things off. - A guy who is traumatized from his breakup so he doesn't want to continue the hobbies he did with his ex. - A guy who jumped to the conclusion that a girl didn't want a second date because she didn't reply to his message (he's so wrong). - A guy who was on a date where the girl was just scrolling on her phone as if he wasn't even there (he actually handled it pretty well). Subscribe for more Reddit dating stories, dating advice for men, and dating tips. Message me or support the show: https://linktr.ee/roycalvin Dating lessons from this episode: How to overcome approach anxiety: practice talking to women more often. Freezing up when a woman responds positively is common when you do not have much experience approaching. The best way to get better is to practice more, assume she will respond well, and stop treating silence like failure.What to say after approaching a woman: keep the conversation moving. If she smiles, turns toward you, and says something friendly, anything is better than giving up and walking away. Even a simple or imperfect follow-up keeps the interaction alive.Assume women will want to talk to you when you approach them. A positive mindset helps you stay prepared instead of freezing. Approaching with the assumption that she may enjoy the conversation makes it easier to respond naturally.Use simple conversation starters when talking to women in bars or social settings. You do not need a scripted routine, but it helps to have easy topics ready. Commenting on the venue, the music, the dance floor, or something she is wearing can keep the conversation moving.Dating therapists and dating coaches may not fix your dating life, especially female ones. Spending money on dating therapy does not guarantee results, especially if the advice does not help men create attraction. Men should be cautious about paying for advice that does not lead to real dating improvement.Being liked by women is not the same as creating sexual attraction. A man can be friendly, hygienic, and easy to talk to while still failing to create romantic or sexual interest. To change that, he needs to approach women directly, ask them out, and stop relying only on being liked.If your dating mindset is not working, you need to change your approach. If the same beliefs and behaviors keep producing the same results, refusing to consider a different strategy will keep you stuck. Being open-minded about dating advice is necessary when your current approach is failing.How to enjoy hobbies after a breakup: create new memories with new people. If a hobby reminds you of an ex, avoiding it forever can make the breakup control more of your life. Going with friends and creating new memories can help separate the hobby from the old relationship.How to ask for a second date: send a clear invitation, not a vague text. Saying “we should do this again sometime” is not the same as asking for a second date. If you want to see her again, suggest a specific day or plan instead of waiting for her to take the lead.Phone use during a first date is disrespectful, but call it out smoothly. If a woman keeps scrolling while you are talking, it is fair to stop and address it. A calmer line like “I’m waiting until you’re finished on your phone” may give the date a better chance of continuing than a harsher confrontation.

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There's a lot of clueless guys asking for dating advice on Reddit, and there's just as many people providing them with terrible guidance. If I replied to their posts with the advice they actually need, I'd just get banned and be told that I'm an idiot by the other commenters (despite having been on more dates with more women than all of them combined). That's where this podcast comes in. I'm checking out the most cringeworthy, clueless dating and relationship posts from Reddit to provide REAL dating advice for men that the gatekeepers of the internet don't want you to know.

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