So there is a bartender that works at two bars my friends and I frequent. He's known my two friends for a while now, and they always talk and whatnot when we get to the bar, but as I'm the "new" girl and a bit shy to boot, I haven't actually talked to Cole the Bartender ever.

One night, Marissa, who seems to always have money to get her hair and nails done as well as shopping but not enough to chip in for gas or pay for my or Clare's cover since we drive her EVERYWHERE because she doesn't have a car, got wasted. Really wasted. I mean, we were at this particular bar because a band that we know was playing (they're a pretty decent cover band and we know all the members) so when she got up on stage with them to dance, it was ok....even tho she passed the acceptable two-song limit we had collectively decided upon for other drunk girls. That she was up there for more than two songs signified that she was pretty gone.

Not wanting to babysit her anymore than I had to and looking for Clare, I went to the back bar where Cole works. It's in another room which is awesome because it's much quieter when the door's shut - makes ordering a drink much easier. As I was scanning the room, Cole got my attention and I asked him if he'd seen Clare. He said he hadn't and asked me what drink I wanted. I declined because I was DD as usual (this is not a complaint, I'm not a fan of getting drunk) so he handed me a water bottle. I handed it back, saying I was alright, but thanking him. Some chick walks up to the bar to engage him conversation and somehow whatever they were talking about morphs into a conversation about music and I get involved. And then suddenly the chick is gone and Cole and I are chatting about covers of popular songs done in a different style (think Jennie Owens Black Hot in Herre, Alannis' Humps or The Fray's Heartless etc.). I have never spoken to Cole for this long and I thought nothing of it. People talk; it's one of the reasons we have mouths.

The following day Clare is all over me about what we talked about and what I thought about it. Awfully fishy behavior, so I know she's up to something. Turns out Cole messaged her via fb, something he NEVER does asking about "what's up with" me. So now I have to be tactful. There is nothing wrong with Cole, he's kinda awesome based on what we've seen at the bars - he's nice, he's funny, he's kinda cute. There's not much not to like other than the fact that I don't know him and no one knows how old he is. He jokes about it, but no one really knows. So I have to handle this so that I don't throw off our awesome social dynamic at the bars.

The next time we see Cole, I got free drinks. I tried to pay him but he wouldn't take it. And after his shift he came and sat down next to me and stuck around. This is rare for him. So I'm sitting between him and Marissa trying to include her in the conversation because I'm honestly not sure I want the attention. Maybe if I didn't know he was interested I would have been more relaxed but I know for a fact that once he sat down I took up less space at the bar by curling up in my seat. Marissa is no help whatsoever. She's on her phone tweeting about being a 5th wheel (Clare and her bf were there) and then a 3rd wheel (after Clare+bf left. Clare told me about this as she gets Marissa's tweets forwarded to her phone) and when Cole brings the discussion over to a tv show that I'm working on catching up on, I move out of the way so he and Marissa can talk about it and I won't over hear anything. When we girls chew the night over the following day and I bring up Marissa's lack of help, she responds that she was trying to keep the conversation between me and Cole. Clare and I held back on calling her bullshit out, but that's another can of worms that I refuse to open right now.

After our second bar chat, Cole friends me on fb and we chat via messages about a few things. He brings up the possibility of hanging out and I figure it couldn't hurt so I give him my number so we can discuss it. This leads to lots of texting and finally an agreement to either check out an open mic night (provided his friend was going to be running it) or The Hangover. I was definitely hoping for open mic night. Movies are dangerous territory - you never know when the "friend" you're seeing the film with is going to try to make a move and then you're stuck. The days leading up to the hangout were full of my friends calling it a date and me fervently hoping for the open mic night to pull through.

You can tell that things didn't work out, can't you?

The dude Cole wanted to see wasn't going to be there that night so when I got home from watching my uncle's dog I made sure to put on a clean tshirt and a pair of jeans. I was not going to be concerned about what I looked like provided that there wasn't a lot of skin showing (I had been wearing capris and a tank top).

I did send out a few texts requesting friends to coincidentally meet up with us at the movie. No one wanted to provide me with a convenient c-block.

We met at the theater and this supposedly hugely popular movie was being screened to four people: Cole, myself, and two other guys. We got great seats but it's a shame I couldn't focus on the movie as much as I was focusing on not being close to him or mimicking his movements. Again, I was super nervous about this. If I screwed it up it wasn't just going to be between Cole and I - it was going to screw up the whole social dynamic at the bar between my friends and our bartender.

After the movie we stood in the parking lot and chatted again about music. We argued over the importance of lyrics to a song - I maintain that they sometimes make or break a song, he doesn't care about them and thusly doesn't pay any attention to them. He starts asking me about my job and I explain what I do and how it's part time. He can't believe how few hours I work during a week. He asks me what I want to do with my life and I say I have no idea (it's true) but that I'm not overly concerned; I'll figure it out eventually. He agrees that I have time, I'm young. "Exactly," I say, "it's not like I'm...[pause to consider an age that won't offend him = no clue what to say] How old ARE you?"

He tells me.

I think that I held it together. I don't think I flinched. I don't think I said anything offensive. We stood around chatting for a while longer, I let him borrow a cd, and then I figured it was late enough for me to plead dried out contacts and tiredness from dog sitting as an excuse to leave. We hugged and parted.

The whole drive home, however, I kept muttering his age over and over to myself. My friends and I had him pegged to an age range of late twenties - early thirties. I was floored to find out he was 39. 30-freaking-9 years old.

I'm only 23. I know that I can't turn my nose up to older men, but I was creeped out. I think it is more due to him KNOWING how old I was going into this while holding his age back than it is due to the fact he was in high school while I was in a cradle.

We haven't talked much since then. I sent him a message the other day to let him know that we were going to the bar tonight for Clare's birthday and that he better have his voice warmed up for some karaoke, but he's been quiet and I'm not entirely sure what to do. We can totally be friends. I'm ok with that idea, but anything romantic is out of the question for me as far as he's concerned. I sincerely hope that tonight isn't awkward at all and that we play nice together. I'm not really concerned that we won't, but you really can't predict how the other person will behave. I, for one, plan on just being my regular old self.

But I have to ask....am I being ridiculous to let a 16 year age difference matter?

When I was a junior in college I got lonely. And after griping to two friends (they were roommates) who were younger than me about how I wished I knew more guys they managed to get me to meet one.

Let's call him Kirk.

Kirk lived off campus and had transferred to our school from RIT during my sophomore year. He was my age and was lumped in with my class except due to the transfer he was a semester short. He was an art major. And he played lacrosse.

My friend Alice invited us over to his place to watch a movie. It was nice of him to not mind that she was taking me with her. I wouldn't say that we hit it off right away, but he seemed nice and I wasn't going to say no to another meeting. And I didn't. We went to the zoo in December because he had to observe primates for his anthropology class and it was fun. We chatted the whole time, I helped him observe, we looked at the big cats, freaked out at the creepy cheetah staring us down like we were its next snack, and he held my hand on our way back to the car   Needless to say I was pleased with this outing since it was nearing the end of fall semester and I had been studying/freaking out over upcoming finals.

During finals week we got to know each other really well. You know, in that heavy-petting kind of way. I was drawn to him because I had never met anyone like him. He was a jock but he was artistic (yay stereotypes!). He liked anime (*cough*nerd*cough*...oh wait, I've watched my fair share, lol) and listened to techno. And he spoke to his cat in babytalk. I think the day he sang to his cat to the tune of the Copacabana was the day I rather literally fell in love with him.

But I was also drawn to his upbringing. He was Christian, which was nice for me since I was as well, so he understood about not having sex - even though he himself was not a virgin. He came out and admitted that sex was his only real big vice - he didn't drink and he didn't smoke, which was also a bit of a turn on for me since I wasn't big on drinking and am not a fan of smoking. We were totally upfront about what was going on. He said he wasn't looking for a relationship of long standing and I agreed to that. Even though I did like him like crazy. Which, of course, he knew anyway.

Things went along great with only a slight hiccup when he was a bit worried about seeing me, knowing that I liked him so much. I straightened it out saying that I understood where he was coming from, that I was a big girl and knew - because he TOLD me - that I wasn't going to be his girlfriend. I said we were just having fun and I was in no way going to inhibit my romantic pursuits because of him.

And I didn't. I actually got walked over by another guy, but that's a different story, lol.

Kirk and I just kinda fell into this open and comfortable sort of friends with benefits relationship. I would have visited him during the summer if he hadn't gone to Japan on a school sponsored trip. Or managed to get a girlfriend almost immediately after coming back on US soil. Yeah...THAT was an awesome turn of events.

I remember the first time I saw her I was almost physically ill. Which was weird because by that point I was a senior and had my own boyfriend with whom I was happy. Kirk and I still chatted online all the time and I learned about how he met her: he cheated on his high school gf with her, dated her during their freshman year at RIT, and then dumped her but remained friends.

Whenever we chatted we usually ended up bitching and moaning about our respective relationships. Mine was rapidly turning into some kind of passive-agressive split where my bf (who had issues with being antisocial) began not wanting to be around me for stretches of time. Kirk's gf was just five and a half hours away up in NY. And she was sick.

And this was the crux of every complaint Kirk made to me. He was lonely. She was far away. She was ill and tired and in and out of the hospital and didn't want to talk. And he noticed that a lot of his friends were no longer his friends. A lot of people stopped talking to him. Girls would act weird around him because he had a girlfriend. Soon, I was the only person he could talk to about it. And I listened because I was his friend.

As the year progressed I dated one of Kirk's roommates and for a bit I wasn't allowed to talk to him because my new bf thought it was awkward. And then we broke up and Kirk was back in my life (though technically he'd never left it cause there was no feasible way I couldn't come in contact with him). And then I graduated and began looking for a job (still am).

Over this past summer Kirk had to find a new apartment for school. He had to work several jobs. And his gf had to be moved to Philadelphia in hopes of a lung transplant. He was constantly driving down to my neck of the woods to visit her and would call me around 10 every sunday night to keep him company as he traveled back home so he could work the next day. I would always ask how she was doing and was always glad when the report was positive. She gave him the option to dump her because she had a feeling her life might take on the pattern of only occassional visits out of the hospital but he didn't want to. I was hoping she'd get better soon because I wanted this to work out for him; he always seemed to be getting a raw deal.

And then he began pestering me to move out towards my alma mater and get an apartment with him. So to shut him up I paid a visit while I was visiting my roommates in Harrisburg. And we hung out like old times. It was great. We got some food, we wandered the mall, he joked about getting me on What Not to Wear, we went mini-golfing and watched some movies on TV. He let the apartment idea drop.

For a week. And then he was back at it. And I explained that it would be a bad idea because we are too comfortable around each other. Maybe that doesn't make any sense at first, but think of how you'd feel if your SO was so comfortable with their roommate of the opposite gender that sharing a bed wasn't an issue and was encouraged by your SO? I know I would be a little nervous about it and I didn't want to put him in any compromising position - he had enough to deal with anyway. He didn't see it my way, of course, but there was nothing he could do about it save get a single bedroom apartment and hope they take cats.

School started for him (last semester! Yay!) and added another hardship to his life. It quickly became consumed with class, homework, work, helping the lacrosse team's practice, study, and driving to Philly to visit his gf who was too ill to have the transplant but was still in the hospital in hopes of getting well enough to have the operation.

And then his birthday began to creep up and no one was going to celebrate with him. So I drove out there since I believe you should always celebrate your birthday, no matter how small the celebration is. I promised that we would rent whatever movies he wanted. Then I received a call from the two friends who had introduced us; they were planning on helping him celebrate as well and wanted to know what I was planning. We quickly put our efforts in tandem and Kirk was able to have a mini-party with pizza, movies, and ice cream cake.

The girls left and it was time for bed and I gave him a massage to help him sleep like I did back when we were juniors. It was late, we were both tired, he was lonely and during the night there was a little friendly molestation of the upper torso. I left for home in the morning and we didn't talk until the next day when he asked if I thought that was grounds for cheating. I told him that I had a sneaky suspicion that it was. He said he wouldn't tell but from now on it might not be a good idea to have a sleepover. I totally agreed and apologized for the situation.

Last week we had what I thought was a joking conversation about how we'd never work out as a couple. I didn't think we'd work and Kirk didn't understand my thinking. I told him that I liked to dress up and go out, that I would get on his nerves by being so cheerful and goofy, and that based on junior year we would never get any sleep. His response was that he liked getting dressed up, he didn't like to sleep and he hated being unhappy.

I have worked hard to get myself acclimated to the idea of being his friend. He loves his gf and is devoted to her - he'd have to be to keep driving down to visit her even when he couldn't financially afford to or have the time. Although I laughed his answer off, it bothered me because I know he finds me attractive. So I didn't talk to him for a week. It really wasn't a big deal, I just needed to get my head straight.

I texted him last night (Sunday) to ask how his weekend went - I had had a good one with my roommates and was ready to share our adventures with him - and was shocked to recieve the news that his girlfriend had died of an infection in the hospital earlier that day. I immediately called him to make sure he was alright and if he had asked me to I would've driven to his apartment in the middle of the night. I told him that if he ever needed to talk he could call me and he thanked me, said there wasn't much to talk about, but I could message him if I wanted to. This week he'll be going up to NY to help her family make preparations and attend the services.

I want to be his friend in this. I'm heartsick for him and wish I could just give him a hug for as long as he'd let me, but I know he's not a talker. And I know he needs his space. And this whole situation is kind of weird for me.

The next time we hang out, how should I behave? How do I make sure I am responding properly to him? What do I do if he makes a pass (I know that sounds like it should be the last thing in the world to worry about, but he has never hid his attraction)? Or am I just being silly to worry?