How do I ask this person out?

He’s staff, I’m a volunteer

Love Letters

Q. I am a woman with a crush. Last year, a former co-worker 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

A. 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 others, 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 have managed to date people from work (years ago), but in one case I ran 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

READERS RESPOND:

He’s full time and you’re a volunteer so the organizational chart is murky at best. Find out what he drinks and bring him a coffee, but do it slyly.

THEKIDSRALLRIGHT

Do you know this guy’s status or anyone who does? That’d be my first question. Are there other social events for the organization as a whole? It may be easier to go to those and attempt to chat this guy up there, for more intel.

PENSEUSE

If he’s a volunteer program coordinator, something like that where he has direct advisory responsibility over volunteers, yeah, that could be a problem. If not, you could just say “I wanted to ask you for coffee but didn’t know if you’re allowed to socialize with volunteers.” And take it from there.

DANGLEPARTICIPLE

I would have a conversation with him and see if he wants to continue talking or wants to disengage so he can attend to other things. Just because he’s friendly doesn’t mean he’s interested. A lot of this is built up in your mind so I think you need to rein it in a bit. If he wants to continue talking, you have a similar interest; you can always say you are going to a game, art gallery, movie, whatever, and invite him along.

JSMUS

Agree with Meredith on respecting his work environment and boundaries, but you both are adults so I think casually asking if he’d be interested in grabbing a coffee is OK. Keep it cool. If it does progress, don’t let on at this organization. No one else’s business and you want to respect his work boundaries.

BKLYNMOM

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