Don’t ask out a co-worker until you are friends first

I have a co-worker/boss with whom I am infatuated/in love. She was recently “dumped” (her words) by her live-in boyfriend/ common-law spouse.

I don’t want to miss a chance to explore a romance with her, but I don’t want to be “the rebound guy” either.

How long before I say anything? Confused Worker

It’s never too soon to say something nice, like “Hope you’re doing OK.” But it’s way too soon to ask if her breakup gives you a chance.

Since she’s openly using the word “dumped,” she’s bound to be hurting, even if she covers it up at work.

She’s likely unsure herself about whether she’s furious with the guy, now thinks he’s a jerk, or wants to get back together.

Be empathetic, but not intrusive. She doesn’t owe you “the story.” When you see her, say something light about something at work, or yes, even comment on the weather.

Be friendly enough that, in a few weeks, you can suggest a coffee together during a break, then lunch several weeks later.

Build a friendship first before trying to proceed further.

Get past “infatuation” — a way of dreaming about love rather than experiencing it — to learn more about her and whether you have more in common than the same workplace and your crush.

Remember that, as much as you don’t want to later find out you’re just her “rebound guy,” she’s also going to be naturally wary of being hurt again. Reader’s commentary: Regarding whether to take a “last chance” with someone first loved 20 years prior (Sept. 28):

Reader: “I hope this person won’t wait to declare continued love.

“I was 19, a girl from a small town working for the summer so I could return to university. I planned on getting out of that small town, finishing school, and travelling the world.

“The love of my life walked into my life the first day on the job. Like it happens in the movies, he ‘had me at hello.’ ”

“Two years into our romance I was offered a chance to spend a year in another country. He gave me a religious silver medal to keep me safe on my journey. I broke my own heart when I left him behind. Worse, I broke his heart.

“In one of his letters, he informed me he had a new girlfriend. When I returned home he was still dating her. I continued to travel all over the world. Yet memories of him followed me everywhere.

“Occasionally, we’d reconnected via phone, cards, through mutual friends. We always seemed to run into one another. Each time, I knew I still loved him.

“Eventually, we both married others. When my first child arrived, he called. When his first-born arrived, I called.

“We attended each other’s parents’ funerals.

“Twenty years later, we bumped into one another again, still married to others, the children grown up. I still loved him but couldn’t tell him.

“I always pictured us meeting again in our golden years. I would tell him, ‘I still love you.’

“Forty-one years later, on a summer day, many miles away on a highway, there was a car accident and the driver succumbed to his injuries. It was him. A friend called me with the tragic news. My heart broke. The silver medal he gave me, a photo from years ago, the memories, are all that’s left.

“Your advice-seeker needs to tell the woman now that he still loves her.” Tip of the day Infatuation is only the dream of being in love, not the experience of it. Read Ellie Monday to Saturday. Email ellie@thestar.ca or visit her website, ellieadvice.com. Follow @ellieadvice.