Skip to content
Join our Newsletter
Join our Newsletter

Ask Lisi: Ultra wealthy friend clueless about her privilege

Every once in a while, I get annoyed with the constant chatter about trips taken and planned, events happening and her “so, so busy” life doing nothing
Lisi Tesher, for Ask Ellie column

Dear Lisi: My friend was raised with a lot of money. She never wanted for anything and had every opportunity she could ever dream of. She’s not showy or ostentatious, and she’s not obnoxiously spoiled. But she is pretty clueless as to how the rest of the planet — even the upper middle class — live.

For starters, she’s never really held a job nor has her husband. He dabbles in this and that, but he has no career ambition, so just does things to get him out of the house and looking busy. She gets excited about something, takes courses but then never follows through.

And she’s always so busy with her own stuff. She’s lovely enough, warm, kind, good-hearted, which is why we’re friends. But every once in a while, I get annoyed with the constant chatter about trips taken and planned, events happening and her “so, so busy” life doing nothing.

I don’t want to end the friendship, so how do I deal with it when I feel like I need to be as far away from her as possible?

Suffocated by wealth

Take a break. Be so, so busy yourself with your own life, no matter what that entails. When you feel fulfilled within yourself, not pressured financially (because even if you don’t have a lot of money, pressure comes and goes), and have space in your heart, give her a call.

Hopefully your friendship can find other things to talk about, other ways to connect and laugh. But if the conversation starts to get money-heavy and you feel yourself getting anxious, say something. It could be as simple as “Hey, can we talk about something else?”

If she’s really clueless, you may have to spell it out for her.

Dear Lisi: I recently exited a relationship I had been in for just over a year. It was a difficult relationship, but there were a lot of joys as well. Both of us had not been in a serious relationship for more than 10 years. I was travelling and highly involved in education but when I met my ex, I was finally ready to settle down.

I would like to start dating again, just meeting people and making friendships. Nothing serious as of yet because I am still grieving my break up. Would you recommend a dating site? My concern is that I met my ex on a particular site I like, and I’m now afraid my ex will see me on it.

Maybe I shouldn’t worry so much and just focus on letting my ex go. This site seems the best for me right now because I am not looking for anything serious, but of course, if things materialize over time when meeting someone, then who knows?

Ready Again

You said you are still grieving your break up. Give yourself time! Do some soul searching and figure out why the relationship was so difficult, but you still stayed in it for a year. Learn from your experiences. Hang out with friends and friends of friends.

When you’re ready, you’ll know which route to go. There are a multitude of dating sites out there. No harm in trying a new one to avoid the ex.

FEEDBACK regarding the woman who wanted to travel while her husband didn’t (Dec. 21):

Reader 1 - “Good advice but I would also add, get him checked out by his doctor for medical problems like anemia, low thyroid or testosterone or depression.”

Reader 2 – “Your answer shows a misunderstanding of an elderly person’s mind set. The reason he doesn’t want to go anywhere is because he is comfortable in his home and doesn’t want to leave it.

“Find a like-minded person, single, widow or divorcee to travel with. The husband doesn’t mind his wife going away without him, so the problem is solved. And there will be lots of experiences to talk about. My late husband and I made separate trips with great success.

“If no suitable travel buddies come to mind, there are many singletons’ travel trips available or perhaps contact someone through friends.”

Lisi – You’ve basically reiterated my response, adding that the woman find others with whom to travel. Great idea, though not the issue. I wasn’t suggesting she cajole her husband into travel. My point was that she needn’t go away for so long, and she could see if maybe he would like to join in on a trip. Compromise was my focus so they maintain their long-lasting relationship.

Ellie Tesher and Lisi Tesher are advice columnists for the Star and based in Toronto. Send your relationship questions via email: or

push icon
Be the first to read breaking stories. Enable push notifications on your device. Disable anytime.
No thanks