[IntrovertedNotShy]

Hi April, so recently I had my work Christmas party and before it a few of us met up for a drink. There was this woman there, a colleague, someone I had noticed before, and liked, but until that evening had never talked to, and from that point on I’ve developed a crush for her.

There was a bit of playful banter throughout the night but I’ll put that down to drink than anything else. Though it included buying me a drink or two, a chat and being playful with my phone.

My problem is that I don’t know her and I never get a chance to get to talk to her. Sometimes there are opportunities where I could but the odds are very low.

I could add her on social media and etc but I would prefer to come across as confident and I believe face to face is better, especially as we work in the same place.

I know what I want to say, I just don’t know how to approach her. I want to invite her out for a drink or a coffee and get to know her, see if we get along.

It’s also a confidence thing that stops me from approaching her whilst she’s with other people. I know there will never be a perfect time to do so, however I would appreciate your opinion.

Thank you so much for any help you can give.

[AskApril Masini]

Get her phone number from a friend or a friend of a friend — tell them you’re interested in her, and you’d like her number. This will get back to her, which is a good thing because she may be excited to hear from you. Then call her up and tell her you really enjoyed seeing her at the party and you wish you’d had a chance to talk to her. Then let her respond. This is how you get the conversation going. You can ask her about the party, if she had a good time, how her holiday is and was, and then ask if she’d like to have dinner with you. It’s that simple! 😉

Your instinct about not using social media is correct — it’s really not an attractive way to contact someone you want to make a good impression on. So, forget that — and do get her number, call her up, have a conversation and ask her to have dinner with you. 😉

[Sally]

When you barely know someone, it feels like there’s this tiny window where you can make a move without it being weird… and you don’t want to miss it or come off too strong. But honestly, those little moments from the Christmas party the drinks, the banter, her playing with your phone that wasn’t nothing. People don’t bother with that unless they’re at least curious.
You don’t need the perfect moment. You just need a simple one where she’s not deep in a group conversation. Even a quick “hey, got a minute?” works. Keep it light. Just say you enjoyed talking to her at the party and ask if she’d want to grab a coffee sometime. That’s it. No big speech.
You’ll feel better taking the shot than sitting with the what-if. And she’ll probably appreciate the honesty.

[Tara]

This isn’t a timing problem, a strategy problem, or a “confidence thing.” This is you hiding behind overthinking because you’re afraid of a clean yes or a clean no.
You’re not confused. You’re scared. Scared to interrupt. Scared to look awkward. Scared to be rejected in a workplace where your ego has nowhere to hide. So instead, you fantasize, analyze banter, and debate social media etiquette like that’s doing anything other than wasting your time.

She bought you drinks. She joked with you. That’s not a marriage proposal, but it’s more than zero. And right now you’re stuck at zero because you won’t open your mouth.

Let me dismantle your excuses. There will never be a perfect moment. Ever. If you’re waiting for her to be alone, perfectly relaxed, and gazing at you like a rom-com cue, you’ll die waiting. Adults create moments. Children wait for permission.

Adding her on social media to “test the waters” is cowardly. It screams insecurity and avoidance. If you work together, face-to-face is the only move that doesn’t make you look like a background character in your own life.

Here’s exactly what you do: you catch her for thirty seconds, not five minutes, not a monologue. You say, calmly and directly, “Hey, I enjoyed talking to you at the Christmas party. I’d like to grab a coffee or a drink with you. Are you free this week?” Then you shut up.
No rambling. No disclaimers. No self-deprecation. No “if that’s okay.” You ask. She answers. You move accordingly.

[Member]

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