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I recently caught up with an old friend of mine at a party who I knew had a crush on me when we were younger (Middle school young then, I'm 23 now, she's 21) I shared the feelings but never asked her out, and I told her that at the party and she seemed to be really happy about it but also frustrated I never asked her out - and told me she "knew it" all along at least four times. We hung out for the rest of the party, she told me she's single and described what she is looking for in a guy (Its a huge list of superficial things, but lots of the personality traits line up with me and we both have similar wants in a relationship.) I jokingly said "Well what if I asked you out now?" and she smirked and put a finger to her mouth and said "I'd probably say no." She hung out with me for the rest of the night after that, which gave me mixed signals. Throughout the night she also brought up lots of old memories, ranging from fun stuff we did to the times when we were quite intimate together. She also did trust me with a lot of personal info that I was never expecting to have shared with me, and long after the party was over she and I just hung out and talked until 4AM in her car.
I am a bit unsure of what to do now, as I have feelings for her again and I find her attractive in all sorts of ways but I am concerned that she is 'guy shopping'. Some mutual friends told me that she hangs out with lots of dudes and is trying to find the 'right one' and that she is off put by the tiniest of red flags; which to me is a major red flag lamo. She also told me this and kept mentioning a bunch of other guys she was talking too, which I did not like at all. She was recently cheated on, so I can't blame her for being cautious with guys, but at the same time she seems very desperate to find a new boyfriend and in my opinion is putting herself in situations where she will probably get hurt again by another jerk. I'm really confused on that "probably not" as to me that means friend zoned.
What Girls Said
Your best (and only reasonable) option is to keep your fingers off from her.
She indicated that she did not want to go out on a date. That should be enough for you to pull back, mainly in view of the fact that she is testing multiple men. That is not really a good sign and a person that behaves like that is not really trustworthy in my opinion.
All her red flags seem to be a real issue for you and you seem to want to ignore them since you would like to pursue with that relationship.
I think you would regret ignoring them if you get indeed together with her because her character will not change just because she dates you.
She probably does have some attraction toward you, but the “I’d probably say no” comment sounds more like emotional caution and uncertainty than a clear rejection. At the same time, she also sounds like someone who is still healing, heavily evaluating options, and possibly chasing an idealized relationship, so you should be careful not to romanticize her too quickly. Instead of trying to decode every signal, ask her on a simple low pressure date once, and if her answer is still vague or mixed, take that as your sign to step back.
You are talking like a 13-year-old. You are not ready for dating right now.