I let crushes fester

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Hi Meredith,

I have a repetitive problem where I get intense crushes on people I'm friends with and then never say anything about it (but continue to let the crush fester until it becomes creepy/unhealthy). I've always told myself that I'd tell the person I was interested if I ever had a sign they were interested as well, but I can't seem to determine what counts as “enough” to make a move, and nothing ever feels like enough.

I've got the beginnings of a crush on a friend I carpool to work with a couple times a week. He's the perfect candidate for my bad habit of silently pining for people – and that's kind of what I assumed was bound to happen, but I just realized that for once I caught it early. I could still say or do something casual before I've spent enough time pining that any expression of interest comes out with the intensity and absurdity of Mr. Darcy's first proposal.

But the thing is, he hasn't given me any indication that he's interested. We have a fun time in the 1.5 hours of driving we spend together on days we go into the office, but we never spend time together or talk outside that time period. I don't want to make things awkward to the extent that I lose the friendship (or my ride to work). So I guess I wondering whether I should make a move or move on – and how does one go about either of those things in a way that won’t harm the friendship?

– Crushed

Is this the first time Mr. Darcy has been mentioned in Love Letters? If so, congrats – and thank you for reminding me that this exists.

This would be great time for you to practice stopping a fixation before it starts. Telling him how you feel is a risk (of a ride, specifically), but these Darcy disclosures don't have to be all or nothing.

Instead of holding up a massive poster that says, "I like you; do you like me?," ask him if he wants to hang out for a drink, meal, walk, or whatever. I'm sure you talk about interests during those car rides. Find out if he wants to do one of the things you talk about, then go from there.

If you get to that next step and it seems like you both had fun, ask him if it might count as a date. At that point, make your interest clear and tell him there's no pressure. Remember you can always stop nervous-talking after that. It's easier to get an answer when you're silent and listening.

If you don't get to that step because he's busy, tell him you'd love to hang out whenever. Then see if he initiates. If not, consider that a real no and move on.

Also know that if all of this fails and gets awkward, you can find another ride. It probably won't come to that, but let's remember it's the ride you're risking most of all. If the two of you only hang out in the car, he's not a close friend.

Don't overdo it in your brain and decide he's perfect before you know what he is, in real life, as a possible partner. Ask the question about plans. That's Step 1. You can't get to any other step without the first.

– Meredith

Readers? How do you ask someone out like this? Can you offer up some not-so-awkward ideas?