How do I ask this person out on a date?

What questions about relationships (or almost relationships) have been on your mind?

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I am a woman with a crush. Last year, a former coworker invited me to volunteer with her. I continue to enjoy the experience; the tasks are fun, it's nice to feel useful, and I love catching up with my friend. Since Day 1, I've been noticing a member of the staff. He is funny, kind, and smart – not to mention handsome. Even though I didn't actually get to speak to him until several months in, his warm eyes and gentle manner caught my attention right away. I think he might like me too, but I'm not sure what to do next. Are volunteers allowed to invite staff to hang out? Would he get in trouble if something got going between us (fingers crossed)? And, most importantly, how can I signal that I want to get better acquainted, and maybe even go on a date, without making him feel uncomfortable at work?

– Amorous volunteer

I have no idea what policies might be in place for staff at this organization. I would imagine they're similar to rules at any other workplace – that people do meet and fall in love, but employees are instructed to pay attention to power dynamics, disclosure, etc., even with volunteers.

That said, having coffee to get to know someone better is not a huge deal, and it might answer some of your questions about this man. Can you start with that? You could ask him to get a beverage with no expectations for more. If he says no to coffee with no follow-up, that's an answer. Then you can show him you respect boundaries by not asking again. If he says yes, well, you'll take it from there and see if coffee leads to better plans.

Volunteering is a great way to meet people. A lot of people do it to help, but also to expand their social circles. I would guess he knows that. I'm so glad you're worried about his comfort at work, but it's OK to ask for someone's time.

Readers, can you share how you brought a work/volunteering relationship to the next level? I did it once years ago, but I happened to run into a work acquaintance at a bar, so the geography did the work for us.

How did you figure out if warm feelings at work could be something more? Tips?

- Meredith