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Episode 006: "I lent my boyfriend money. He took it to a casino."

Episode 006: “I Lent My Boyfriend Money. He Took It to a Casino.”



Today’s episode really has everything. Piggy and I exchanging loving compliments and deep insights—then following it up with sex jokes, and a little off-mic shrieking as this poor Redditor describes her situation.

A young college student lent her older boyfriend money for food and student loans… yet he somehow ends up at a casino.

Hmm… yes, we might have something to say about this one.

Today’s question

“My [21F] boyfriend [28M] owes me over $100 and I found out he went gambling last night.

“My boyfriend never really has money and still lives with his parents. I recently paid for a $40 dinner, spent over $50 on groceries for him this month, and gave him $80 for food and weed. He says he will pay me back next paycheck (and he usually does) but he is always asking for cash.

“We are very honest with each other and we see each other almost every day. He said that he’s flat broke and I even paid off a loan for him, but I found out from a mutual friend that he went to a casino last night…

“Now, I have no problem with him going out, and he has every right to go out and have fun, but he lives HOURS away from the casino and I am a college student with very little money and have a hard time paying my bills with the money I keep lending him, and he goes off to this casino which is a very expensive place. Whenever he goes out when he’s broke he always said that his friends are buying, but I don’t know which friend he could be talking about. He tells me everything too, so it’s very unusual for him to go on a day trip and not invite me or tell me about it since we go everywhere together and we always communicate.

“We have been together for 3 years and have a strong relationship and I spend the night at his house like 4 days a week even though he lives nearly 30 miles away. He’s not a moocher. I don’t buy him everything and we will usually go 50/50 on things. Should I confront him about why he’s not paying me back and going on an expensive trip that’s 3+ hours away from his town?”

As always, all thanks for this episode go to our loyal, amazing Patreon donors. They sponsored this episode with precious money we would never allow within a casino.

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12 thoughts to “Episode 006: “I Lent My Boyfriend Money. He Took It to a Casino.””

  1. Preach, y’all. I have a couple book recommendations for letter writer:
    – Facing Love Addiction by Pia Mellody
    – Is it love or is it addiction? by Brenda Schaeffer
    – Dodging Energy Vampires by Dr. Christine Northrup

    Letter writer, sending love to you. Take the next $100 and spend it on therapy, on your precious self.

    I was in a similar boat as you when I was in my early 20’s. Thank god, one of my best friends stopped me when I described an emotionally vacant, dismissive male as “kind”. My best friend said, “Hannah, you need to redefine kind.” They were right.

    Start the journey ❤️

  2. Letter writer, I hope you understand this guy is using you – for money and company… he’s not a good boyfriend. get your money from him if possible and then dump him and move on. There are much more nicer guys out there for nice person like you. You don’t need a pathetic loser who cant support himself and on top of that, using you.

    I’m glad you got someone that gave a hint on where your money is going.

  3. WAIT WHAT? He’s not a moocher? He has every right to go out and have fun? Please, please, please tell this girl to get out of that relationship. If you are giving him money, he is a moocher. If he lives at home, he is a moocher. If he takes your money and gambles it, he is a moocher. He has NO right to go out and have fun if he can’t pay for it. He is using her and he is using his friends.

    I send this person love and support. She is an enabler and being abused and she doesn’t recognize it.

  4. Well, if you have any plans in the future, ditch him or make him stop. Not being responsible with money now, when he doesn’t have a family is one thing, but it will almost surely become worse over the years, if you start a family. Gambling addiction is not OK.

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