Skip to content

Ask Lisi: Should I go on a date with my crush from high school?

If there’s a spark, great. Go for it! If there isn’t, you’ll have caught up with someone from your past.

Dear Lisi: When I was a teenager, I had a major crush on one of my friend’s older brothers. She was a good friend, and we spent a lot of time together. Whenever she’d invite me for a sleepover, I would jump at the chance because that meant time with her big brother in the same house.

One night, he came home late and was loud coming upstairs. As he passed by our room, our eyes met, and he smiled. My friend was sound asleep as I slipped out of bed and followed him into the bathroom. We kissed for what seemed like hours.

The next morning, he was still asleep when we left for the day. For whatever reason, I didn’t see him again for a few months. When I did, he brushed past me on his way out and barely said hello. I was devastated.

Fast forward 20 years and I bumped into him at a coffee shop. We had the nicest conversation, but he had no memory of that night we kissed! And he told me he always had a crush on me but thought his sister would kill him if he acted on it.

The craziest thing is that we both are newly single. Now I’m wondering if we should go on a date and see if the crush is still there for both of us. What do you think?

Teenage Crush

I absolutely think you should go on one date. Why not? Nothing horrible can come from spending a few hours with this guy. You have lots to talk about: the high school years, his parents, his sister, and what you’ve both been up to these past two decades.

If there’s a spark, great. Go for it! If there isn’t, you’ll have caught up with someone from your past, and maybe even closed a door you didn’t realize was slightly ajar.

Dear Lisi: My wife is going through menopause but won’t admit it. She has hot flashes in the night; she’s moody, irritable, and gaining weight in places she never gained before. She also has a very low to non-existent libido.

I’ve tried to talk to her, but she says she’s not feeling well, and probably coming down with something. She’s changed the way she dresses to hide her body and pretends that she’s not hot at night. I’m on her side and want to help her go through this life stage with as little discomfort as possible.

How can I get her to open up?

Caring Husband

Be honest and open with her. Tell her that you love her no matter what, and that you want to help relieve any discomfort she is having.

Tell her that although you’re not a doctor, or a woman, you have an idea of what is going on in her body and you’d like to help her.

Do some research on your own about menopause and how diet, exercise, and hormone therapy can help women. If there are small helpful changes you can make, go for it.

Whatever you do, tread lightly as she obviously has some shame and insecurity regarding this stage of her life.

FEEDBACK regarding the woman whose best friend dumped her without an explanation (March 25):

Reader — “I think your advice was spot on for the person who lost their BFF. I liked the way you began your advice with empathy about their situation as well.

“Yours is an advice column first but recognizing and acknowledging someone’s suffering gives comfort to a confusing and painful situation.”

FEEDBACK Regarding the friends with the newly famous son (March 24):

Reader – “Something the writer hasn’t considered: a celebrity is often targeted by tabloids, and reporters from tabloids will contact friends and family trying to get dirty laundry aired about the celebrity.

“The boy’s parents may be very nervous if tabloid reporters are hounding those close to them. They may be backing away from people in an effort (in my opinion, misguided) to maintain some privacy or even have some feeling of control.”

Lisi – That is very true! But I’m not sure it’s misguided. I’m reading Spare by Prince Harry, who mentions the paparazzi and the tabloids, and the negative impact they had on his life from a very young age.

And then every relationship he ever had, every foolish mistake ever made, every time he erred, the tabloids would have a field day.

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