My friend and I both worked at a temp agency the job ended and we are currently not working. last week I received a free bet on a gambling app I use I won $3,000 I put up $2,000 because I am moving next month the rest of the money I used for bills, my daughters Christmas presents and I gave my friend $250 to buy his son Christmas presents. as soon as I gave him the money he gambled and lost the $250 I only have $100 in spending money and he is asking me to go into my savings so he could get his son Christmas presents and he would pay me back on the first. I really don’t want to give him the money and risk him not giving me my money back or gambling the money away as soon as I give it to him. He has put me in a awkward situation I don’t really know what to do I asked him to just get the gifts on the 1st and he keeps telling me it wouldn’t be the same as getting him gifts for Christmas Day. I feel bad but he’s not a single parent his child Will still receive gifts on Christmas Day from his mom if I don’t give my friend the money. He has been at my house for the 4 days and he has been constantly bringing this situation up we could be having a good conversation or playing around and he’ll randomly say “you got me for Christmas” he’s leaving today and decided to make a cart on Amazon and ask if the amount was good before I even agreed to give him the money. I’m really annoyed with the situation and I’m not sure what to do.
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Should I get him a Christmas gift?
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Do not do it. It's his fault that he gambled away the $250 you gave him. You just got lucky when you won the $3,000, he didn't. So it's not your responsibility to cover his loss. You gave him the $250 out of the goodness of your heart the first time, don't put yourself out of any more money to cover his expense. You said he's not a single parent so it's your responsibility even less.
Tell him no and to let it go.
Don't lend him money unless you would be ok not being repaid. You might reasonably lend him $100 or so, or just ask him what his kid's number 1 wish is and get that.
Just say "No."