Can I ask her out again? Should I?

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matty2345 asks:

A few months ago the girl I like was flirting with me, i.e. looking at me a lot, laughing, touching me, etc. I told her I like her and she said she has a boyfriend, and she’s not sure if she likes me more than a friend. She doesn’t have a boyfriend anymore and has come back to flirting with me, she called me baby, said she misses me, touches me a lot, looks at me, etc.

Am I right not to ask her out again? My feeling is that if flirting the 1st time didn’t mean anything why would it this time? She was the one with a boyfriend right? So she should now make a move on me since she rejected me? Also I work with her and don’t want make things awkward again if she rejects me again?


Demetrius says:

If you’re a busy guy like me, you value straight answers early so here goes: You should ask her out again. Everything else you mentioned is irrelevant.

Not enough for you? Okay, fine, let’s address your concerns point by point. They are:

  • Am I right not to ask her out again?
  • My feeling is that if flirting the 1st time didn’t mean anything why would it this time?
  • She was the one with a boyfriend right?
  • So she should now make a move on me since she rejected me?
  • Also I work with her and don’t want make things awkward again if she rejects me again?

First things first, yes you are right to not ask her out again if by “right” you mean “silly”. The world on a larger scale, and your love life on a micro scale,  so not operate on a system of “right” or “wrong”. Would you be right if you waited for her to ask you out? Yes, but also no. Would you be right if you seized your opportunity and asked her out? Yes, but also no. If you want to be proactive and you like her, ask her out. Don’t be silly here.

Next up, the idea that the first time she was flirting meant nothing is just straight up wrong. It meant something, something she just could not act upon at the time. The flirting was real, there was clearly some amount of attraction behind it, but she also couldn’t act upon it because she had a boyfriend. If someone who is currently in a relationship says they might like you as more than just a friend and they’re flirting with you that means something. If you don’t believe me, try to put yourself in his shoes, assume you found out that your girlfriend was flirting with a guy and telling him that she might like him as more than a friend. How would you feel? It’s a rhetorical, you don’t have to answer.

Yes, she had a boyfriend. What’s your point? She HAD a boyfriend, now she doesn’t. Get over it, guy.

While it’s true that she had a boyfriend, and it’s also true that you asked her out and she rejected you, let me refer you to my first point about “right”. It’s not like having the moral high ground is going to help you. If you think she should ask you out because you asked her out first and she had a boyfriend, by all means proceed to be silly and wait for opportunity to knock. If you’re smart, you’d realize that women tend to expect men to take the initiative in dating, regardless of what came before. She’s showing you through some serious flirting that she’s interested and wants you to ask her out. Waiting for her to do the “right” thing is only leaving the door open for your competition to swoop in and steal your shot.

The work thing is a valid concern but at this point, you might as well go for it. You’re already flirting like crazy and you’re both clearly into each other, so it might be just as awkward if you don’t make a move. Seriously, seize this very clear, very open opportunity and thank me later.

Good Luck Out There.

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