Scrounging bestie overdue for reality check

DEAR MISS LONELYHEARTS: I’m almost 40, and one of my closest friends who was jobless for three years is once again earning decent money again — but she’s still acting like she’s broke!

I don’t care how people spend their money, but she still expects me to pay for her. For instance, if we go out for lunch, she’ll ask if we can do a 75-25 split, with her paying the lower amount. She also comes to potlucks with nothing to share, and then has the nerve to ask to take food home. She will also ask me to cover something and promise to pay me back, but then I have to hound her for weeks to get the money!

But it really took the cake recently when we went to a concert and she asked me to cover her ticket. Then she bought two T-shirts at the merch table! It feels underhanded to me — and insulting to my intelligence. It also feels weird to have to bring it up to her. We’ve been besties since high school —many, many years ago. Please help.

— Taking Advantage, Riverbend

Dear Taking Advantage: This old friend is not just trying to take advantage, she’s doing it blatantly and knows that you know! She may have become a bit too accustomed to everybody paying her way, in life — and you were one of the biggest donors.

It’s time you told her the gravy train has come to a halt — especially since she has a good job and is still asking for freebies. Point out to her that it feels like scamming now, and it’s an insult to your intelligence. She may drop you now as a buddy, but nobody needs that kind of friend.

Dear Miss Lonelyhearts: My dad was a drinker and abusive for all my childhood and into my young adult life. I stopped talking to him 20 years ago, and I just found out from my mother that he’s dying from cancer.

He wants to reconnect with me, but I don’t care if he lives or dies. He was so mean to my mother, my siblings and me — so violent! I just don’t care to hear his fake apologies or whatever he has in mind.

My younger brother is going to see him and is pressuring me to go with him. No! I don’t want to go. Does that make me a bad person?

— So Sick of Cruel Man, Sturgeon Creek

Dear So Sick: You don’t owe your cruel father any last visits or reconnection. Explain your reasoning to your brother very clearly, giving him some examples of his previous vicious behaviours toward you. Tell your sibling you understand he “needs to do what he needs to do.” Reconnecting just isn’t for you, and never will be.

Be prepared for your dying father to have made an “about turn” as he faces the end, so your brother may get a totally different version of the cruel man you experienced. Make sure your brother knows you aren’t cutting him off because of his decision, and that you’ll always be there to talk with him.

Dear Miss Lonelyhearts: We packed up early at our lake this year because my wife is heading out of province for her high school reunion. I’m staying home with the kids. Other people she knows are taking their wives and husbands, but she didn’t ask me to accompany her.

I already know why! The jerk who dumped her the day after their graduation is going to be there. I’ve seen the graduation pictures in my wife’s yearbook and looked him up on Facebook. She talks about him casually from time to time, and I always hate it.

I thought she’d want me to be there, to show him that she did much better by marrying me. I make at least twice the money and still have a fit body and all my hair, unlike him. Also, I have loved and respected this woman every day since I met her. Help me understand this!

— Left Out, Southwestern Manitoba

Dear Left Out: Sometimes people go to their high school reunions out of sheer curiosity. And some people don’t take their mates because they want to the freedom to talk to whomever they wish, for as long as they wish and not have to include their present partners.

Unfortunately for them, the old loves they want to chat with often don’t look the same anymore and don’t have much to share conversation-wise, as they have moved on. Also, they may have their mates in tow, who don’t enjoy conversations where they really don’t know anything about the people.

Please send your questions and comments to lovecoach@hotmail.com or Miss Lonelyhearts c/o the Winnipeg Free Press, 1355 Mountain Ave., Winnipeg, MB, R2X 3B6.