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Posted

To support myself in med school I work at Barnes and Noble. The holiday rush has started so I see a TON of older women.

 

Anyways, I started talking to one I was helping out a couple months ago. We talked for about 15 minutes. I remember her name and added her on Facebook when I got home. I figured it was creepy, but I had nothing to lose.

 

Fast forward to 3 months later. I'm in her town for a wedding (she lives 8 hours away) and I message her asking if she wants to meet up. I figure I'd get a reply that just says "hey, i'm busy but thanks.' Instead, she sends "I'm out of town this weekend, but I'll be in your town in September x, wanna get coffee?" I figure this initiative is good.

 

September x comes around and we meet up in my town. The BEST date Ive ever had. Funny, smart, sexy. She asked me if I liked older women and if this was a date, to which I laughed and said "do you want it to be?" and she laughed and I cant remember what she said. I screwed up by not answering "yes," unfortunately.

 

Afterwards she gave me a kiss on the cheek and messaged me that night saying I'm "awesome" and shed "love to do it again." Also she paid for the coffee even though I insisted.

 

I messaged her to see if she was around for the holidays in my town. She said she was and she’d let me know! Does she want to be intimate? How can I tell? I'm not sure if she was just being nice or if she actually liked me.

 

Also I live w my parents and when she visits she stays w her parents, so how do we get privacy?

 

I am 25, shes 45, btw

Posted
September x comes around and we meet up in my town. The BEST date Ive ever had. Funny, smart, sexy. She asked me if I liked older women and if this was a date, to which I laughed and said "do you want it to be?" and she laughed and I cant remember what she said. I screwed up by not answering "yes," unfortunately.

 

If you do like older women, you should have said "yes" to that particular question. As for the second question, not sure how it would of turned out if you did say "yes" because she might have feel pressured. But since she offered to get coffee, I doubt that. Don't over-analyze this situation, just have fun and hopefully you guys meet-up again.

 

 

Also I live w my parents and when she visits she stays w her parents, so how do we get privacy?

 

Maybe you two can use the stock room of the Barnes & Noble you work at. Or rent a hotel room. Or don't worry about it until it comes up.

Posted
Afterwards she gave me a kiss on the cheek and messaged me that night saying I'm "awesome" and shed "love to do it again."

 

She couldn't be much more obvious... kiss her like you mean it, dude!

 

And don't wait on her to tell you to get a room!

Posted

This is not 100%...but normally when an older woman asks "do you like older women?" she is hoping you say yes because she is interested in younger men. I never ask that question because I'm not.

 

Also, when a woman asks is this a date? Normally it is because she hopes it is.

 

Unless she asked it with a concerned look on her face. Then she is worried YOU think its a date.

 

Good luck!

  • Like 1
Posted

At this point I do not know if she wants to be intimate. You had 1 coffee date for heaven's sake three months ago in September.

 

I think she might have been receptive to another date had you asked her out 2 months ago. Now she probably thinks you don't find her attractive & if you call her now she will be suspicious that all you want is sex. That should not prevent you from asking her but understand the obstacles you face.

  • Author
Posted
At this point I do not know if she wants to be intimate. You had 1 coffee date for heaven's sake three months ago in September.

 

I think she might have been receptive to another date had you asked her out 2 months ago. Now she probably thinks you don't find her attractive & if you call her now she will be suspicious that all you want is sex. That should not prevent you from asking her but understand the obstacles you face.

 

I asked her if she'd be around for the holidays, and she said yes and she'd let me know closer to the date.

Posted

Yes, she definitely likes you. Next time you meet up, make sure to tell her you find her funny, smart, sexy, etc.

Posted

This is my favorite thread for today.

 

When you meet up with her next time, try being a little bolder and more flirtatious, and you two might have some serious sexy-fun times.

  • Author
Posted
This is my favorite thread for today.

 

When you meet up with her next time, try being a little bolder and more flirtatious, and you two might have some serious sexy-fun times.

 

why is this your favorite thread?

  • Author
Posted

Do I book a hotel room before and take her there afterwards? Or suggest it to her at the time?

Posted
why is this your favorite thread?

 

Because it's adorable. And also because the sexy cougar / younger guy thing intrigues me a lot, but I have to wait a while more before I can qualify as a cougar.

Posted

The youngest guy I went out with was 15 years my junior, believe me I couldn't figure out what he wanted from an older girl like me when he could have much younger girls (he was a very good-looking lawyer). So we danced around the attraction we felt for some time with me trying to figure out if he just enjoyed my company or we could really take it to the next level. The questions she asked were cues enough for you that she is interested, but very cautious because you might just be after her to add a notch on your bedpost. I say go for it, you can learn so much from this relationship, but bear in mind that you are both at different stages in your lives and this might be difficult to reconcile.

Posted

I agree with Danda and with donnivan. I think she is interested but since you were a bit hesitant you might want to give it one more meetup before you try to be physical otherwise she might think you just want to conquer and move on so to speak. But definitely this time don't be hesitant with the flirting.

Posted

Personally, I would find someone closer to my area. And I have no idea why a 45 y/o woman would want to date a 25 y/o man who lives with his parents.

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