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How to ask a former co-worker out without making it awkward?


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Posted

I just found out a former coworker of mine is finally single. I always had a thing for her before she quit. The only contact I have with her is on Facebook. Since she is single now, I would like to take her out on a date but I am not sure how to approach her without making it awkward or desperate. Messaging her on Facebook would be weird since I've never message her in the past.

 

I need some suggestions to get a date with this girl. Help LoveShack community.

Posted

Start a conversation first. Just a hi how are you is fine. Then say "would you like to go out for a drink?"

 

It really is that easy.

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Posted

Would it better if I wait until the holidays are over or ask her today, which is Christmas Day, to see if she wants to go have a drink? I know people are with busy and with their families during the holiday.

Posted

Message her and tell her you wanted to wish her a merry Christmas and see how she's been. Take it from there. It's not awkward to ask over Facebook. I'm a female and this has happened to myself numerous times (guys asking me out to dinner, etc).

Posted

I agree with the christmas thing. Or you could just say things are different around work without her and you wanted to catch up. I say just go for it, you don't work together anymore so really there is no reason to be cautious.

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Posted

Thanks for the tip. I message her on facebook so I hope this goes somewhere.

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Posted

Quick update: She replied to my message and we chatted for a little. She was out of town and the flow of our conversation was not going smoothly so I did not get a chance to ask her out. She got home late last night, but she did message me this morning. We chatted more, but it was just small talks about how the tires from her car popped and she didn't get home til late last night. Our conversation stopped when she went to the tire shop.

 

So what now, I don't want her to think I am being clingy or needy so I am not going to message her tonight. But maybe tomorrow to see how she's doing and if she have any plans for New Years eve. Would it a good idea to ask if she wants to hang out on New Years eve? Or should I wait til the holidays are over to ask her out?

Posted
Quick update: She replied to my message and we chatted for a little. She was out of town and the flow of our conversation was not going smoothly so I did not get a chance to ask her out. She got home late last night, but she did message me this morning. We chatted more, but it was just small talks about how the tires from her car popped and she didn't get home til late last night. Our conversation stopped when she went to the tire shop.

 

So what now, I don't want her to think I am being clingy or needy so I am not going to message her tonight. But maybe tomorrow to see how she's doing and if she have any plans for New Years eve. Would it a good idea to ask if she wants to hang out on New Years eve? Or should I wait til the holidays are over to ask her out?

 

Captain: Forget NYE. You send her message about you and her catching up. Use the phrase >> catch up.

 

Something like: "Hey Jane, hope everything with the car worked out. After the holiday it would be great to catch up. How about coffee?"

 

Boom!

 

You're not really asking her out on a date. It's just two former co-workers getting together to "catch up" on things. If she agrees, meet her and work your charms. You could parlay it into a real date. ;)

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