Awkward Situtation

[IcecreamLove]

Sorry this is a LONG story but I would appreciate some opinions.

 

There used to be a boy that I liked that worked with me, let me call him, "Max". I worked with him for about 2 or 3 years and we were good friends since the start. We would take lunches together, have all these inside jokes, just be on our own planet. I had a crush on him, sigh.

 

A girl I worked with ended up trying to date him and we joked about it because we both hated her. Then came "Jill." Jill is one of those girls that jumps from guy to guy. When she first met me, she was telling me about her boyfriend in another state, a week later, she is crying that she cheated on him, etc. She ended up pulling me aside one day claiming she had a secret to tell me. The secret was that she was dating Max for about a month or so. She took his virginity.

 

He ended up getting fired at my job but Jill remained. I never really liked Jill. She is kind of lazy, asks off all the time, blabs her personal problems all over, always makes my time at work more difficult. She talks to me a lot though and we text on and off if she is having a bad day.

 

Jill and Max broke up... eventually and things got really awkward. Max started working at a new store and we barely kept in touch. I talked more to Jill but only because I was being polite and worked with her. She ended up getting two jobs, her other job, at the other store with Max. Drama. Max quit that place and now works somewhere else. She always said negative things like he just sits at home and drinks all the time, he is so depressed, he loved her too much, so on and so.

 

Fast forward to now. I keep in touch with Max, through texting. Although we have never hanged out, outside of work, Monday I was free and asked him if he wanted to hang out with me, and said yes. So he picked me up Monday, and he just drove around, and caught up a lot.

 

He eventually parked at this game preserve, and we went hiking up one of the mountains. We lost the trail and figured the fastest way was up, and even though I had to stop a lot of times, we made it, talking back and forth, then adventured the way back down. That was that.

 

We sat at the picnic tables, talked some more, people watched, joked around, got hungry, and went to a pizza place. He paid for all my food. I tried to force money on him and he kept giving it back, whatever, his loss. He took the food to go, and drove back to the game preserve, parking at this lake.

 

We spent about 3 hours in his car. Just sitting together. Talking about the woods and joked about rapists that probably hide out in the woods, and vegetarian monsters. It kept getting darker and darker. I was getting cold; he offered me a hoodie of his. But as happy and as innocent I want all of that to sound, there was a lot of awkward sexual tension between us. I mean, we were both talking about sexual things, our bodies, times he's had sex in his car, fake moaning, trying to find the hottest songs on his ipod, and freaking ourselves out about some rapist all with this joking undertone to it.

 

I am not that sexually experienced. And I am terribly shy. Everytime I get put into these situtations I have no idea what to do. Everytime he would let his mind drift into the gutter, I would just laugh. Eventually around ten, I put my seatbelt back on, and was like, "well I guess the rapist is never coming I'll just put my seatbelt back on..." he put his on, we drove back home. I was kind of happy and comfortable in his sweater, but he asked it back when I got out of the car which was boo I could not even muster a hug, lean over for a kiss, anything I just said bye, and mumbling about missing him, because I did. He told me it was fun.

 

The whole experience has left me very confused. We took some pictures together too. I added them on Facebook, didn't tag him, and blocked Jill from the album. I cannot help but think, he wanted to do something with me. Like I said being in these situations before, it has never been easy. My first boyfriend wanted a really physical relationship with me, and I kept pushing off his advances and getting all giggly when we kissed. Eventually he saw he was not getting in my pants, and just dumped me instead. But everytime in my head, I think I will handle things differently, be mature, be grown up and instead I ruin it for myself by crawling back into my shell.

 

I used to write in a journal when Jill and Max were dating. I remember I wrote that I was kind of relieved that they were dating, since the fantasy was out of my system but I also felt like, she beat me to the punch. Max was better with me, I was just too shy to ask. Besides, if Jill found out what happened Monday, or people at work found out I would NEVER live it down. I am thinking about asking him to hang out again sometime next week. Except it would be me driving, to his actual house instead. What should I do next time?

[LDRohnos]

Just be honest with him. Being shy is fine but ultimately you're going to get passed up on opportunities unless you act on them.

[abitbroken]

I think you did the right thing by not giving in. Since you have not seen him in a long time, take it slow. He was not entitled to sex or even making out just because you were together for much of the day. I think you have to make it clear to him that you are interested by asking him out one more time and then its up to him to reciprocate, but I would take it slow. when the conversation turns to sex, what about talking about how you prefer gentleman and doesn't he think making out is for when people are dating for awhile and in love and see what he says. If you want to kiss him, well then go for it, but I would take everything slow because if he is talking about sex like that - then that is what is on his mind. Just be careful and don't do what you don't want.

 

Also, what about asking him to something that doesn't involve going to eachother's houses like a movie? or ice cream? or meet at a local octoberfest?

[catfeeder]

Phones work both ways. You invited him out this time. I'd leave the contact--and next invitation--up to Max.

 

If you focus too hard on driving relationships where you want them to go, you lose opportunities for valuable information--such as what someone will do of his own volition.

 

I can't speak for you, but I'd want to know that. I'd pipe down and find out by letting him show me.