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What's stopping you from saying: "Hey - from now on, we go 'Dutch'" - I know men don't use that term but just say from now on you will each pay for your own stuff.
You said: "Things were fine until I started going out for drinks and food with him."
So I guess you enjoyed the things you did with him that didn't involve drinks and food. Why not go back to doing those things?
It seems pretty clear he doesn't have the money to pay for food and drinks, and believes or knows that you do have the money. (As you said, you can "easily afford" it) so I think this will be the norm from now on since it's already happened a few times. I think all you can do is try to go back to the activities that don't involve food and drink for a while to get back to how things used to be, where you're not opening your wallet.
So I made a new friend who moved to my town recently. He's going through a transitional period in his life and seems to be struggling financially. We have a lot in common and we hit it off instantly. He almost always initiates contact and asks me to hangout with him.
Things were fine until I started going out for drinks and food with him. He always asks me to cover up for him which I don't mind. What pisses me off is that when I get something for like 10 dollars he would go on and order several items, costing me at least 100 with no remorse at all. This happened on two occasions. And the last time we hung out, he asked me to buy him a drink, which I agreed to thinking that he would pay for the other items he had ordered, but he left without paying for anything.
Now the money isn't the problem for me because it's something I can easily afford. But if there's one thing I hate it's being taken advantage of. And knowing that maybe this person doesn't enjoy my company at all and probably befriended me for my money.
I really like this person and enjoy his company. But at the same time I don't want a user in my life. I would really like you advice on this. Should I see if this happens for the third time, or should I drop him now? What would be the best way do it?
With the best intentions you've set the stage for both of you. If you want that to change, you'll have to change the script. He certainly may be short on funds, but that's no excuse to take advantage of you. HE needs to be honest about that.
The next time he asks to go out, you need to test the waters in some way as was suggested. Go someplace that doesn't involve paying for anything. Go someplace less expensive (so neither of you are embarrassed if he can't pay his share) and say "OK, but we split the check 50/50." Say you don't have a lot of cash on you. Don't bring your cc. Whatever it takes. If he questions you about this, be honest. If he wants to be up front about it he'll accept it. If not, he'll probably turn on you and be gone.
Gross. What the hell kind of a person does that? If I knew I couldn't afford something, or that someone would have to "cover for me", I'd get the cheapest thing on the menu. Or not go out at all . This guy's trying to live the good life on your dime. I agree with those who suggested you take no more than $10 and see what he does.
Gee, OP, have you ever said to him, "Can you please pay for your own items?"
Honestly, I think so many problems could be solved if people, you know, just ASKED. Instead, we are somehow afraid of offending ... what, someone who is using us to the tune of hundreds of dollars (or more?!)? OP, seriously, what is keeping you from ASKING him about this?!!
So I made a new friend who moved to my town recently. He's going through a transitional period in his life and seems to be struggling financially. We have a lot in common and we hit it off instantly. He almost always initiates contact and asks me to hangout with him.....
I really like this person and enjoy his company. But at the same time I don't want a user in my life. I would really like you advice on this. Should I see if this happens for the third time, or should I drop him now? What would be the best way do it?
First, I would tell him straight out that paying for drinks when you go out while he is trying to get on his feet is OK. But not food, unless you invite him for a meal.
Second, see how it goes with him "getting on his feet," some people never seem to make it. If two or three months after he gets settled into a job he is still always expecting you to pay his drink tab, then I'd start being unavailable for at least fifty percent of his let's-go-out calls.
What kind of place does this guy live in and how does he pay his rent/bills if he's unemployed? Does he have ANY money at all?
Everyone said what I was thinking at first, (a user) and still do think he's a user, but then I also started to wonder if he was hungry and hadn't eaten for a day or two... or more.
If so, what he could have and should have ordered was a cheaper meal of fries and a burger. He ran up a $100 bill, so how many drinks DID he order and was he eating shrimp and and expensive cut of steak?
So I made a new friend who moved to my town recently. He's going through a transitional period in his life and seems to be struggling financially. We have a lot in common and we hit it off instantly. He almost always initiates contact and asks me to hangout with him.
Things were fine until I started going out for drinks and food with him. He always asks me to cover up for him which I don't mind. What pisses me off is that when I get something for like 10 dollars he would go on and order several items, costing me at least 100 with no remorse at all. This happened on two occasions. And the last time we hung out, he asked me to buy him a drink, which I agreed to thinking that he would pay for the other items he had ordered, but he left without paying for anything.
Now the money isn't the problem for me because it's something I can easily afford. But if there's one thing I hate it's being taken advantage of. And knowing that maybe this person doesn't enjoy my company at all and probably befriended me for my money.
I really like this person and enjoy his company. But at the same time I don't want a user in my life. I would really like you advice on this. Should I see if this happens for the third time, or should I drop him now? What would be the best way do it?
This is not a friend....This is someone who recognizes you as a "mark" Someone who allows him/herself to be used.
Simply stop answering his calls.
Ask yourself. Why on earth would anyone allow themselves to be used like this? Clearly you recognize that you are being used. Why would you continue?
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. This guy's trying to live the good life on your dime. I agree with those who suggested you take no more than $10 and see what he does.
OP, seriously, what is keeping you from ASKING him about this?!!
