To support myself in med school I work at Barnes and Noble.The holiday rush has started so I see a ton of women. I remember her name and added her on Facebook when I got home.Anyways, I started talking to one I was helping out a couple months ago. I figured it was creepy, but I had nothing to lose. I'm in her town for a wedding (she lives 8 hours away) and I message her asking if she wants to meet up. 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?

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It turned out we both loved coffee and I was over the moon at finding someone who was addicted as I was. I awkwardly ran into my house and didn’t message him for the rest of the week.

We both knew the same people, it was a small town and we liked to talk about who we knew. Fast forward a few months and I considered Jay to be one of my closest friends. But before I had a chance to say anything, he invited me to his house for a family dinner because apparently his parents really wanted to meet the girl he’d been dating.

We talked everyday, met up for coffee, food, had drinks down at the local. Not only did he match my love of coffee, but he loved sushi too. With nothing to do, bored and sick of all the love statuses on Facebook, we met up and decided to have a day of loving ourselves. When he told me this, I almost spat out my coffee all over his face.

He should have been my dream guy, except I didn’t view him like that. Yes, he was a good looking guy, yes I enjoyed spending time with him. For us, this meant a day of sushi and over-priced coffee. I was single and having a whale of a time with one of my best friends. I had no idea we’d been dating and, frankly, the thought sort of terrified me. When did I cross from being friendly to a possible love interest? Is society so messed up that just because I agreed to meet up with this guy on a regular basis, talk frequently and laugh at his sorta funny jokes, this meant he assumed we were dating?

But I didn’t want to kiss him, I didn’t want to rip his shirt off and run my fingers down his back. How could I possibly be dating someone without even realizing it? I suppose we don’t really ask people permission to date anymore: it’s just a natural assumption. I quickly found myself replaying our friendship in my head. It wasn’t even as if I’d been completely oblivious. Can men and women not hang out anymore without it automatically meaning they are dating? I didn’t want to be more than friends and he didn’t want to just be friends.

I’d said a few hundred times how happy I was to be single and not dating anyone at that time. I guess we were just on the wrong page, and it’s a shame, as he was a pretty decent friend.

Maybe one day men and women can agree to be just friends.

I screwed up by not answering "yes," unfortunately. I'm not sure if she was just being nice or if she actually liked me. In my experience, older women know how to ask for what they want. :-) You should run with it and let her know if you want to take things further. Oh, and don't forget to take a condom with you.

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.

He’d once accidentally messaged me on Facebook thinking I was someone else. We met almost every day for a quick coffee and a gossip. The next time we met for coffee, I had full intentions of clearing up the situation.