“I Regret Dumping Her Because She Never Picked up the Tab”

I was married for 25 years and have been divorced for a year and a half. A year ago, I met a lovely woman and we have had great times, going out dancing and listening to live music. However, she has never picked up a tab, and when I pointed that out to her, she said she could hardly pay her bills. She is on disability but is able to do things. I suggested she maybe get a small part-time job to help with our expenses, and she said she is afraid of losing her health insurance. She sells things on eBay and is able to make a couple of dollars when she has a good sale, but she still doesn’t pick up a check. This bothered me until it came out in a big fight. We both emptied our clothes from each other’s homes. It has been a week and she has already joined a dating site. I feel used and taken for granted, but I have major regrets about breaking up. Any insight would be appreciated. — Feeling Used

 
I don’t think she lied about not being able to afford picking up checks on your dates or about being afraid of losing her health insurance by getting a part-time job (if she even COULD get one). If you were unable to afford the dates you two went on, and you knew she was unable to afford them, a better option than telling her to get a job would have been… you know, going on cheaper dates. You can enjoy someone’s company without spending much or any money.

It doesn’t sound like this woman was using you. Using you for what? To go out dancing and to listen to music? She was doing those things because she liked your company and those were activities that you enjoyed together. Considering that you have regret about breaking up with her, maybe YOU were taking HER for granted. At any rate, what did you expect after you broke up with her? You dated for a year and you dumped her because she couldn’t afford to pay for any of your nights out. She hardly owes you a mourning period. And PS, how do you even know she joined a dating site? If you only know because you were on the dating site yourself and saw her profile, that’s pretty rich. You’re both free agents now and she’s as entitled to find her next date as you are (but you just might want to make sure your next one has a job).

It is 20th-high-school-reunion time. I am one of a very close-knit group of four friends from my high school class. One of us, whom I will refer to as “Bud,” decided to attend the reunion. But Bud decided to go without telling any of the other members of our clique. Bud is not in contact with many, if any, other members of our class other than our group. Our group was stunned that he would go to the reunion in the first place, let alone go without his close friends. He seemingly did not want us there.

We are befuddled and, quite frankly, offended. Does Bud want to “upgrade” his friends? Is he embarrassed by us? Is he trying to distance himself from us? All of us in the group are successful and personable, and there is no reason that we can see as to why he would want to distance himself from us.

Your initial thought may be that he is angling for a girl he had a crush on in high school or something like that, but we attended an all-male school, and Bud, as far as we know, is heterosexual.

Are we making too much of this? My gut is usually right, and my gut tells me that something is wrong. Is Bud a jerk? — One of Four

How are you so close after 20 years of friendship and you can’t say, “Hey, Bud, why didn’t you mention you were going to the reunion?!” That’s a normal thing to say to a friend you’re tight with. And then you could better gauge from his response what the deal was. I did wonder if he might be pursuing a romantic interest that he didn’t want wing men for, and that’s still a possibility even if you all went to an all-male school.

Perhaps Bud isn’t totally straight after all. Or maybe he wanted to network for business opportunities and thought having his close friends around would distract him from that agenda. I don’t know! But it seems odd to jump to the conclusion that something is “wrong” and that Bud is a jerk. It sounds like Bud’s going to his/your high school reunion had literally nothing to do with you and your other two friends. And confirming this would be as easy as simply asking.

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If you have a relationship/dating question I can help answer, you can send me your letters at [email protected].

5 Comments

  1. Anonymous says:

    LW2 sounds like he’s still in high school.

  2. neighborhood disabled person says:

    LW1 doesn’t understand or doesn’t care how SSI or SSDI disability works. You are allowed to have income other than the disability payment each month but only allowed to make up to a certain amount of money. If you were to make more than that, you would no longer qualify to receive disability benefits which include health insurance. So even $1 over the threshold could cause the ex-gf to lose health insurance, yes, and that is a big problem when someone has A DISABILITY.

    LW1 needs to educate themselves and also maybe don’t date a disabled person if LW1’s primary concern is a partner contributing more money to the relationship.

  3. Anonymous says:

    “Offended”, “stunned”, “gut says something is wrong”, that Bud decided to go the the reunion and didn’t inform the others in the group?

  4. Anonymous says:

    “Offended”, “stunned”, “gut says something is wrong”, that Bud decided to go the the reunion and didn’t inform the others in the group? Wow. What a shock that

  5. Sorry. Keeps posting before I was done. “Offended”, “stunned”, “gut says something is wrong”, that Bud decided to go the the reunion and didn’t inform the others in the group? Wow. What a shock that he didn’t tell the others in the group if that’s their attitude! Probably Bud just ran across another classmate who said, “Hey, come to the reunion! I hear [fun classmate is coming, the entertainment is going to be awesome, old teacher X is going to be there]!” or he just read the mailing and thought on a whim that it sounded like it could be fun or interesting to go. But he likely knew his close-knit small group of friends considered reunions to be a weird thing they totally wouldn’t want to go to, “because they weren’t close to any of those other people, so why in the world would any of them even consider doing such a thing?” So rather than cause a lot of uproar in the friend group, he just decided to check it out for himself and give it a shot.

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