r/Advice•
MyPenWroteThis

Want to grab lunch with a woman at work I would like to know. What's the play here?

Me and this women haven't had much chance to speak other than a couple chance run-ins. She seems really nice and is very attractive. I have no idea if she's single or not.

We have only ever said hi a couple times, and spoke briefly at a company summit in NYC earlier this year.

Today I ran into her in the hallway and after a minute of chit chat, she went about her way and as she left I said "hey we should grab lunch some time" and she said "yeah sure!". However, in hindsight, it's clear it would've been almost impossible for her to decline without it being awkward.

That small chit chat, she did seem okay stopping to talk a little bit, but perhaps was being polite. I don't have a great read on her yet, but I wouldn't say she seemed uncomfortable or like she didn't want to talk. (I generally have a decent sense with people but I've been wrong before)

Another woman on her direct team I have a friendly relationship with. We already have lunch schedule for next Tuesday and her and I have met for lunch a couple times.

The options I'm considering are below:

  1. Ask the woman I'd like to know if she wants to grab lunch tomorrow via teams chat. Nothing fancy or suggestive, just "Hey there! Want to go to the cafeteria and grab lunch?"

  2. Wait until next week to ask her to lunch on Wednesday or Thursday.

  3. (The option I think MIGHT work more) Ask the woman I'm already going to lunch with if she is down to invite her team. This would include 2 other woman and maybe their boss, a man- but one of those woman is the one I want to talk to.

I don't intend to flirt or anything, just get to know her a little bit and see if I can forge an easy friendship and take it from there. I've been in the professional world for a while and am not concerned I will slip or say anything that could be inappropriate. I get along with people well and rarely have awkward air with anybody.

What are the thoughts, Reddit?!

Posted Dec 4, 2025, 2:33 AM UTC

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