How Do I Pursue This Crush?

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Dear Meredith,

I feel like I have a “Mission Impossible” crush situation. I recently went to my local pharmacy to pick up a prescription I only need once a year. Normally I don’t think much of this task, however the woman who helped me with my order was unbelievably attractive, and now I find myself having the crush of a lifetime.

I’d love to ask this woman out on a date, however I don’t want to do so at her place of work – especially while she has other customers and coworkers around. There is almost no reason to go to the pharmacy section of a store without picking up a prescription, and I don’t have anything to pick up now. I can’t seem to find any way that I would get the opportunity to ask this woman out on a date without running into her on the street. Is there any other approach here?

– Crush of a Lifetime


I’ve brainstormed this for a bit, and my answer, as an advice columnist with allergies, is: decongestants. I have to buy decongestants a few times a year, and they keep them behind the counter because of the pseudoephedrine. Sometimes I talk to the pharmacy staff about which brands they have, how much I should get, etc.

If you go when it’s not busy, you can talk to her about the options. Smile. Be charming. Listen. Thank her for her help. See if there are any vibes whatsoever.

If decongestants aren’t your thing, can also buy a COVID test. Ask her which brand she likes.

If you feel good about the interaction, you can take the next step. Maybe leave her a note with a kind message and your number. Something that tells her you’re interested, but puts the ball in her court. After that, walk away and leave her alone so she knows there’s no pressure to respond.

This feels like a long shot, for the record. Remind yourself that at the moment, your feelings are about her appearance. You don’t know her, right? There’s a difference between thinking someone is super hot and having the “crush of a lifetime.” Don’t make assumptions about who she is before you’ve really met her.

If this doesn’t work, it shouldn’t feel like a big loss. She’s a stranger, not a soul mate.

– Meredith

Readers? Is there any good way to ask someone out while they’re at work? Have you done it? Did it work? What else counts as a “Mission Impossible” crush situation?

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