"I Have Low Self-Esteem and Hate Myself. Why Don't Women Want to Hang Out With Me!?" episode artwork

EPISODE · Dec 6, 2025 · 20 MIN

"I Have Low Self-Esteem and Hate Myself. Why Don't Women Want to Hang Out With Me!?"

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 wants to dump a girl after two dates because she chose a restaurant out of his budget for the next date.- A guy who says he has no self-esteem and doesn't understand why women don't want to meet him.- A needy guy who is upset that the girl he's dating doesn't have big conversations via text (he's overthinking it).- A guy who got some numbers at a party but thinks his conversations were boring.- A guy whose mental health is getting rekt because he gets attached too easily.Subscribe for more Reddit dating stories, dating advice for men, and dating tips.Message me or support the show: https://linktr.ee/roycalvinLessons from this episode:If a woman suggests an expensive date, do not make your budget the main issue. If she plans a restaurant that costs more than you normally spend, it may be better to go this time and take the loss instead of making the third date feel like a money problem. In the future, take the lead on planning dates so you control the cost.Do not let the woman choose every date location. A woman taking initiative is a good sign, but the man should usually lead the date planning. If you let her decide, you may end up in expensive or awkward situations that could have been avoided by choosing the plan yourself.One expensive date does not mean your lifestyles are incompatible. After only two or three dates, do not overthink long-term financial compatibility. Go on more dates, gather more information, and stop trying to decide the whole future from one restaurant suggestion.Dating apps can work, but many women are there for attention and validation. Matching with a woman does not mean she is serious about meeting you. Keep your expectations low, ask her out sooner, and do not treat every match like it is already a real opportunity.Ask women out faster on dating apps instead of texting endlessly. If the conversation is decent, send the invite after a few messages rather than dragging it out. If she ignores the invite, she probably was not going to meet anyway, and you save yourself time.Self-improvement alone will not fix your dating life if you never take action. Working on yourself, hobbies, and life goals is not enough if you still are not asking women out or approaching them in real life. Dating success comes from creating opportunities, not waiting for improvement to magically attract women.A woman who is great in person but bad at texting can still be worth pursuing. If she shows up, has great conversations, and enjoys the dates, her texting habits do not matter much. Judge her by what she does in person, not whether she sends perfect messages between dates.Stop treating slow or minimal texting as ghosting. A woman leaving a goodnight text on read is not ghosting if there is nothing meaningful to reply to. Use texting to set up dates and save your real conversations for when you meet.To make conversations more flirty, focus on not being boring. Do not rely on basic interview questions like “where are you from?” or “what do you do?” early in the conversation. Comment on something in the moment, make her laugh, and let the playful vibe develop naturally.To detach emotionally from dating, get more options and stop overinvesting early. If one woman breaking things off after a few dates ruins your mental health, you are getting attached too fast. Go on more dates, meet more women, and stop imagining a future before the situation is actually serious.

Here's who I'm giving REAL dating advice for men to in this episode:- A guy who wants to dump a girl after two dates because she chose a restaurant out of his budget for the next date.- A guy who says he has no self-esteem and doesn't understand why women don't want to meet him.- A needy guy who is upset that the girl he's dating doesn't have big conversations via text (he's overthinking it).- A guy who got some numbers at a party but thinks his conversations were boring.- A guy whose mental health is getting rekt because he gets attached too easily.Subscribe for more Reddit dating stories, dating advice for men, and dating tips.Message me or support the show: https://linktr.ee/roycalvinLessons from this episode:If a woman suggests an expensive date, do not make your budget the main issue. If she plans a restaurant that costs more than you normally spend, it may be better to go this time and take the loss instead of making the third date feel like a money problem. In the future, take the lead on planning dates so you control the cost.Do not let the woman choose every date location. A woman taking initiative is a good sign, but the man should usually lead the date planning. If you let her decide, you may end up in expensive or awkward situations that could have been avoided by choosing the plan yourself.One expensive date does not mean your lifestyles are incompatible. After only two or three dates, do not overthink long-term financial compatibility. Go on more dates, gather more information, and stop trying to decide the whole future from one restaurant suggestion.Dating apps can work, but many women are there for attention and validation. Matching with a woman does not mean she is serious about meeting you. Keep your expectations low, ask her out sooner, and do not treat every match like it is already a real opportunity.Ask women out faster on dating apps instead of texting endlessly. If the conversation is decent, send the invite after a few messages rather than dragging it out. If she ignores the invite, she probably was not going to meet anyway, and you save yourself time.Self-improvement alone will not fix your dating life if you never take action. Working on yourself, hobbies, and life goals is not enough if you still are not asking women out or approaching them in real life. Dating success comes from creating opportunities, not waiting for improvement to magically attract women.A woman who is great in person but bad at texting can still be worth pursuing. If she shows up, has great conversations, and enjoys the dates, her texting habits do not matter much. Judge her by what she does in person, not whether she sends perfect messages between dates.Stop treating slow or minimal texting as ghosting. A woman leaving a goodnight text on read is not ghosting if there is nothing meaningful to reply to. Use texting to set up dates and save your real conversations for when you meet.To make conversations more flirty, focus on not being boring. Do not rely on basic interview questions like “where are you from?” or “what do you do?” early in the conversation. Comment on something in the moment, make her laugh, and let the playful vibe develop naturally.To detach emotionally from dating, get more options and stop overinvesting early. If one woman breaking things off after a few dates ruins your mental health, you are getting attached too fast. Go on more dates, meet more women, and stop imagining a future before the situation is actually serious.

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"I Have Low Self-Esteem and Hate Myself. Why Don't Women Want to Hang Out With Me!?"

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How long is this episode of You Don’t Know Anything About Women: Dating Stories and Advice?

This episode is 20 minutes long.

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This episode was published on December 6, 2025.

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Here's who I'm giving REAL dating advice for men to in this episode:- A guy who wants to dump a girl after two dates because she chose a restaurant out of his budget for the next date.- A guy who says he has no self-esteem and doesn't understand why...

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