Advice columnist

Adapted from a recent online discussion.

Good day, Carolyn:

I have been in a casual relationship for several months with a man who I consider to be a very close friend. We have occasionally spent the night together but have never had a conversation about it.

I want to tell him about my feelings for him, and let him know that if he doesn’t feel the same or isn’t interested in actually dating, then I can’t continue to be his friend-with-benefits. The problem is, I always chicken out of bringing it up — it just seems too awkward, and I am afraid of facing potential rejection face-to-face.

Do you think it would be okay to write him a letter or e-mail about this instead? That way he could process without being put on the spot, and be able to e-mail me back, which might be easier for him, too, if he has to tell me he’s not interested.

(Nick Galifianakis/For The Washington Post)

I tend to think this is just a really chicken move on my part, but I’m curious to hear your thoughts.

Letter vs. Face-to-Face

My inner over-simplifier wants to point out that if you had solid reasons to believe he felt the same way, then you wouldn’t be so afraid to speak up.

My inner PITA (pain in the abuttcheeks) wants to point out that the first gauge of sufficient maturity and trust to be in a relationship is the courage to take an emotional risk and withstand a painful rejection.

My inner everyone else is queuing up to sound off, too, but you already know that chicken moves are for dance floors, not relationships.

Re: Letter vs. Face-to-Face:

I agree this would probably naturally morph into dating, if he were into it. But I disagree that it is a chicken move to put out awkward relationship ideas by e-mail. Sometimes it does give the e-mail receiver a chance to think it through and answer more thoughtfully.

For example, I would rather be dumped by e-mail than in person because I get a chance to process my initial reaction in private, and then respond. As long as the e-mail is thoughtfully written, I don’t see a problem with using this approach.


Fair enough. I do know I used to hear all the time from people who were horrified by e-mail breakups and other emotional-bomb-droppings, and now I’m just as likely to hear from people arguing the merits of just what you say — allowing people an opportunity to react in private.

Re: Letter:

Many of us would be better off if chicken moves stayed off the dance floor, too.

I include myself in that!

Anonymous 2

Where’s your sense of adventure and abject humiliation. Jeez.

Re: Letter:

Go ahead and write it down. But don’t send it. Use the process of writing to get your thoughts in order, figure out what he might say and have a reaction preplanned to each of the options. That should give you enough courage to do this in person.

Anonymous 3

Or a sense of whether you even “should,” says the columnist who long ago renounced the word “should.” Thanks.

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