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How do I interest her? Should I cut my loses or just be blunt and tell her I want to date her?

Tagged as: Big Questions, Dating, Friends, Trust issues<< Previous question   Next question >>
Question - (23 September 2011) 3 Answers - (Newest, 24 September 2011)
A male United States age 36-40, anonymous writes:

There is this girl who I have been interested in dating for a while. We go to school together and we are pretty close. The only problem is she had a boyfriend for the longest time. Now she is finally single again. I never have been great at dating/ reading women. Long story short, I was talking to her and dropped a hint that I was in town (I live a 1/2 hour away.) and that it would be great if I knew a place to eat there.

Ok so she says there are plenty of great places to eat there and that we should get dinner together soon. I am thinking this is a good thing. So we setting on Friday to get dinner then she says this "Great - I can update you on this new boy that I've hung out with."

So wtf! I have no idea what to think now. I do want to date this girl. I am still meeting her tomorrow for dinner and not sure how to move from here.

Should I cut my loses or just be blunt and tell her I want to date her.

Or something else?

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A male reader, Sageoldguy1465 United States +, writes (24 September 2011):

Sageoldguy1465 agony auntI suggest you keep your mouth shut.... be an attentive and listening "date" for the meal.... and let her see what an attentive and listening guy you are..... and try your best to figure out how she's doing with ".... this new boy that I've hung out with."

Afterwards... within a day or two, CALL her, and tell her how nice it was for her to share the meal with you.... AND that you were happy to see her... AND you're glad to hear about her socializing with "...this new boy that I've hung out with."

Then, keep quiet again for a week or more....

Good luck....

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A male reader, Odds United States +, writes (23 September 2011):

Odds agony auntNothing destroys your chances with a girl faster than having a crush but not acting on it. At this point, there's basically no shot. Sorry to break that to you, every guy hast to go through it a few times.

If you want, you can try for a move. Doing it subtly, without saying anything, just going out after dinner for some drinks might work, but just coming out and saying it will not. Chicks dig drama, and drama requires leaving things unsaid.

Go out for dinner, have a nice friendly time, and take it as a lesson for the future: never nurse a crush on a girl who is taken, never hesitate to ask one out if she's single, and never let any girl talk to you about her love life.

You say you've never been great at dating/reading women. Here's something to get you started:

http://www.dearcupid.org/question/how-to-be-attractive-a-beginners-guide-for.html

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A female reader, aunt honesty Ireland +, writes (23 September 2011):

aunt honesty agony auntOK well it sounds to me like she just wanted to meet for dinner as friends and that is all. I guess she didn't read anything in to it other than her just being friendly. I think the best thing that you can do is try and flirt lightly with her, drop hints that you like her and see if she responds to you. If not well then maybe it is best just being blunt with her and ask her would she like to go out on a date sometime. It is best just to ask straight out in these situations and at least then you know where you stand with her. Good Luck.

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