Romantic feelings for boss end in rejection and heartache

She wants to know if they can ever be friends again.

Adapted from a recent online discussion.

Dear Carolyn:

My boss and I formed a very close friendship, which turned into me having feelings for him. I told him around the new year. He confessed that he questioned his feelings, but ultimately he is my boss. We act like business partners, though, with me supervising the staff. Some of our staff call us Mom and Dad.

I put up some boundaries since he rejected me. We strictly work together and don’t go out as friends. I desperately miss our friendship, and I would love to have that back.

I almost talked to him about wanting to renew our friendship, but then I realized he is dating someone. And it hurt to hear that. Because truthfully, I am still holding on to hope. And I am incredibly angry at him for giving me hope. Had he simply rejected me and not held my hand while he told me that he has questioned his feelings for me, I probably would have moved on. But here I am. A 40-plus-year-old women with a crush on my boss.

How do I move past this? Can I ever be his friend? I’ve looked for other jobs, but I love my work.

— Holding On

You can never be his friend.

Your feelings will not be returned.

If you want a romantic partner in your life, then you will need to look for one in someone other than this man.

A no with a flicker of “maybe” in it is just as much of a no as a simple rejection.

I am sorry for all of this. It is obviously way more nuanced than these four statements say it is, certainly for you and maybe even for him, but nuance that brings you nothing is not worth exploring. The face of it is all you need to see: No you can’t; no they won’t; he’s not the guy.

And possibly most important: If your feelings were mutual, then you two probably would have found a way to be together.

Keep loving your work, keep looking for work elsewhere, stomp on every ember of “what if,” and keep reminding yourself that the problem isn’t that he is your boss, it’s that he’s not the guy.

Re: Holding On:

If he’s not the company owner, then he may have more exposure in terms of company policy violation, sexual harassment charges, etc. He may be mindful of all of this. If you want to test this theory, leave for another job. If he reaches out to you then, there may be some romantic future for you two. In any case, leaving may be what you need in order to move on emotionally.

— Anonymous

Re: Holding On:

Her phrasing shows she is putting the blame on him, and it’s true that he should have been more careful about getting so close to a subordinate, but she has a lot of stuff she needs to own. Maybe working to try to own it will help in processing the pain. Any relationship is a gamble, and much more so in the workplace.

— Own It

— Washington Post Writers Group

Talk to us

More in Life

Celebrity chef Gordon Ramsay walks into the Prohibition Grille along Hewitt Avenue in Everett Wednesday Dec. 5, 2012 while reportedly filming an episode of Kitchen Nightmares at the Everett restaurant. (Mark Mulligan / The Herald)
Even more films and TV shows filmed in Snohomish County

Readers point out projects previously missed in this series, from reality television to low-budget indie films.

Daniella Beccaria / for The Herald

15-month-old Kantu attempts to climb a pumpkin at Stocker Farms in Snohomish on Sunday, September 20th, 2015. Stocker Farms offers a U-pick patch, farm animals and a corn maze.
Best pumpkin patch in Snohomish County

You voted, we tallied, here are the results.

The city of Mukilteo is having a naming contest for its new $75,000 RC Mowers R-52, a remote-operated robotic mower. (Submitted photo)
Mukilteo muncher: Name the $75,000 robot mower

The city is having a naming contest for its new sod-slaying, hedge-hogging, forest-clumping, Mr-mow-it-all.

Local musician Alex Johnston, whose newest album "Daylight Fooldream" pairs with short film he made with help from his partner Mikaela Henderson, sits with his morning coffee on Friday, Sept. 15, 2023, at Narrative Coffee in Everett, Washington. (Ryan Berry / The Herald)
Folktronica musician shoots 37-minute visual album on iPhone in Everett

Alex Johnston, 31, describes his music as ”if Coldplay and Bon Iver had a love child.”

Death of parent with child. Piece of paper with parents and children is torn in half.
Helping children cope with the hard realities of divorce

I’s important to set aside one’s feelings and find a way to make this challenging transition as comfortable for children as you can.

In Belgium, each type of beer has its own glass – whether wide, tall, or fluted – to show off its distinct qualities.
Rick Steves’ Europe: Bruges brews lift a weary traveler’s spirits

The Belgian city is a mecca for beer lovers from around the world.

Children’s author Barbara Herkert to lead Story Time at Edmonds Bookshop, Friday September 29th, 9:30-10:00 am!
Author to read her new kids book at Edmonds bookstore

Author Barbara Herkert will read “This Old Madrone Tree” Friday at Edmonds Bookshop.

Can he get the fare difference refunded after he was downgraded?

American Airlines downgrades Thomas Sennett and his family to economy class on their flights from Boston to Phoenix. Why isn’t it refunding the fare difference?

From left, Elora Coble, Carol Richmond, David Hayes, Karli Reinbold, Giovanna Cossalter Walters, Landon Whitbread in a scene from Edmonds Driftwood Players' production of "Murder on the Orient Express." (Dale Sutton / Magic Photography)
Music, theater and more: What’s happening in Snohomish County

Edmonds Driftwood Players opens its 65th season with Agatha Christie’s “Murder on the Orient Express.”

Photo caption: Back-to-school is an ideal time to pick up new habits that help your family reduce waste and learn about resource conservation.
Go green this back-to-school season

It’s an ideal time for the entire family to learn the three Rs — Reduce, Reuse and Recycle.

Some collectibles are found in nature; some imitate them. If it weren’t for the attached figure, this Royal Dux porcelain vase might pass for a real conch shell.
This shell-shaped vase would make a fine souvenir of summer fun

It may not be a real shell, but this art nouveau piece could still evoke fond memories of days at the beach.

Arlington Garden Club celebrating its 90th anniversary

The club has monthly programs for north Snohomish County gardeners and awards scholarships to area students.