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?”

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