I've been interested in a coworker for almost a year. I can tell she has some interest because we flirt back and forth at work. We've also became good friends. There are a few problems though. First of all I'm 37 and she's 24. I don't mind the age difference, but I think she does. Also she dates a lot and gets numbers from guys all the time. She told me she realizes she flirts and is trying to stop. She also told me that she's picky and trying to find the right guy after ending a 3 year relationship.
Anyway, I invited a bunch of coworkers to a Halloween party at a friend's house, and she's the only one who said she could come. We had a lot of fun drinking, dancing, and a lot of flirting back and forth. At the end of the night I tried to kiss her, but she gave me the cheek.
Should I still try to pursue her? Should I apologize for trying to kiss her? Do you think she's interested in me?

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Originally Posted by runobi

I've been interested in a coworker for almost a year. I can tell she has some interest because we flirt back and forth at work. We've also became good friends. There are a few problems though. First of all I'm 37 and she's 24. I don't mind the age difference, but I think she does. Also she dates a lot and gets numbers from guys all the time. She told me she realizes she flirts and is trying to stop. She also told me that she's picky and trying to find the right guy after ending a 3 year relationship.
Anyway, I invited a bunch of coworkers to a Halloween party at a friend's house, and she's the only one who said she could come. We had a lot of fun drinking, dancing, and a lot of flirting back and forth. At the end of the night I tried to kiss her, but she gave me the cheek.
Should I still try to pursue her? Should I apologize for trying to kiss her? Do you think she's interested in me?

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Ok, here is my opinion on this matter. I see two possibilities here. Either she is only interested in you as a friend, or she takes things slowly on a physical level.

See, I did the cheek thing to in the past. In a couple situations, it was because I didn't see them in that light. Then there were other times I did that, because I was shy.

So you see, it could go either way here.

I would suggest letting it go for a while and see what happens.

She must know by now that you are interested in her in that way.

The ball is in her park. I think so any way.

Thanks. Should I at least acknowledge the attempted kiss, and apologize for my bad drunk timing?

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Originally Posted by runobi

Thanks. Should I at least acknowledge the attempted kiss, and apologize for my bad drunk timing?

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If you guys are pretty chummy, then yes I don't see why not.

Just don't make a huge deal about it.

Ok. Thanks. One more question and I'm done. After the no big deal apology, do you think it's a good idea to ask her out right now? Or just wait it out. I know it shouldn't be a big deal, but I like her and I want her to know it. Trying to kiss her while being drunk isn't a great way to show it. Thanks again for your feedback. Obviously I have a tendency to overanalyze these things.

I wouldn't ask her out. I would see what happens. You don't want to come on too strong.

Thanks for your advice.

First off, you don't need to apologize for anything. She knew exactly what you were doing and she responding by giving you what she wanted, the cheek. She could have easily pushed you away. So leave the past in the past. You are overanalyzing.

As for what to do from here on, that's up to you. First off, I ask you to consider the possible consequences. Office romance can get very complicated, to the point that one of you might have to change jobs. Are you willing to face that consequence?

If you are trying to court her, then just keep moving forward. Stop looking back and regretting a decision that you made. You already made it, don't walk backwards.

Are you sure you want to date this girl?

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Originally Posted by runobi

Should I at least acknowledge the attempted kiss, and apologize for my bad drunk timing?

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Hello r:

Hell no! What? You don't think she remembers??

excon

I just don't want to lose a good opportunity. She has most of the qualities I'm looking for. I've been told (and she's shown) that she interested in me, but she's conflicted because of our age difference and she's afraid of rejection. Thanks.

You're not going to have the answers until you confront her about your feelings.

However, again, I only caution that there are consequences to office romance. If you can handle it, then go ahead.

Yes, but I just want to know if I should say anything to her because we work together. And what should I say. I also value our friendship and I don't want there to be any awkwardness at work.

You've been interested for a year and have not asked her out? As a female we want the guys to do the pursuing. You may want to see what happens over the next couple weeks before you make your next move. That being said I don't get how guys just hang out. Aren't you worried someone else will sweep her off her feet? The worst thing she could do when you ask her out is say "No thank you". I've been asked out by guys at work and even though I wasn't interested romantically I acted diplomatic and polite. I'd say go for it instead of wondering.