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I'm just not sure on how to proceed. I don't want to keep pestering him about what's going on.

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Question - (6 October 2008) 2 Answers - (Newest, 8 October 2008)
A female United States age 36-40, anonymous writes:

I'm 21 years old, he's 23. We've known each other since college, and he has graduated and I've left due to financial reasons. We didn't really start to hang out until I moved in across the street from him. At the time, I was casually seeing someone else. It was obvious that he was interested in me, but I was oblivious at the time to it. Once I finally ditched the casual dude, I started flirting with the neighbor.

Our first "romantic" encounter occurred last year in September. We had been talking one night over texts while he was at work (he delivered pizzas) and I was making subtle sexual innuendos that he caught on to. We had planned to meet up at a party later that night. The hosts of the party ended up taking my keys away in efforts to crack down on drinking and driving. I ended up catching a ride with the neighbor. But coincidentally, my house keys were on my car keys. I was locked out of my house. Ended up spending the night with him. Lots of cuddling and talking, but we didn't kiss or anything (I think it was a mutual respect to not disgust each other with our jalapeno cheese fries and garlic cheese fries breaths).

Later things continued to progress well until his best friend revealed to him that he had a thing for me. The neighbor doesn't really talk about things like that to other people, so he felt it was just best to back off of me instead of getting in his best friend's way. I didn't like the best friend in the same manner, and he became upset and it pretty much ruined OUR friendship.

Then the best friend ended up becoming the neighbor's room mate. It put a lot of distance between us, since we couldn't hang out a lot, and the best friend didn't want me around.

I ended up moving across town, but still not too far. It's a small town. I continued to see other guys. I didn't get hung up on him too much.

However, towards the end of the summer this year, things took a complete 180 back into the progressing direction. We started talking a lot more, hanging out, etc. One night he invited me over to his house (while the best friend wasn't there). We chilled and watched tv, talked a bit, caught up. He told me he couldn't sleep as excuse to get me to hang out, yet passed out about an hour after I got there (mind you, passed out physically on me, aww).

The next night, he invites me over again, and during our conversation, he brings up an inside joke about a naked party we once had (which was just three guys in their boxers and me in my bra and panties playing cards - the last time I was actually over at his house, before the previous the night). We end up making out and hooking up that night.

The next day, we don't really talk. A couple days later, I finally ask him what his intentions were. I'm known for being open to casual relationships, no strings attached sort of things. Not slutty, just not a prude either. He hadn't had sex since his fiancee almost two years ago, and he's never done the casual, regular hookups. Which is why I was a little confused on the situation.

He tells me that except for that night we hooked up, he doesn't do casual, and that he's not ready for a serious relationship at the moment. Working on getting his life together and whatnot, that it was a one time thing most likely. Understandable.

Except that it hasn't been just a one time thing.

We continued talking and hanging out, flirting, etc.

A week after our hook up, the opportunity comes up again, and he invites me over. I actually turned him down because I was really tired, had just moved again, and had work in the morning. Later, we end up hooking up again. Another opportunity came up, but he had fell asleep before I got there. Another chance came up, but I fell asleep before I could leave my place. Another chance came up, but I turned it down, again for sleep/work. And then we hooked up again. 7 opportunities in 4.5 weeks. Clearly not a one time thing.

The last time was way different than the others. Usually, we hang out for a minute or two, and then get right to the point. Minor making out, then sex, then stay long enough to catch your breath and get dressed, then leave. Thus the rules and etiquette of casual sex.

The couple days before, he was always calling and texting if I was at work or busy. Calling and texting while he was out with the guys, or out at a party. One night while at a party, he asked me what I was up to 7 times in an hour (while he was 45 minutes away). Like he wanted to talk to me, but didn't have anything to say.

The last time was different. His room mate was home, the one who doesn't like me. Usually his room mate was not there. Then we ended up watching a documentary, just cuddling in his bed for a bit. We talked, he gave me a back rub. Some reason I took off my shirt, I got another back rub. We go back to cuddling and he's just touching me. Brushing his fingers up and down my back, massaging my neck, playing with my hair, little things, until he finds a tickle spot and engage in a tickle war. And then we start making out. But its not the usual "hot steamy kisses" that go from mouth to neck to breasts to sex. This time it was the light sensual kisses that are mouth to jaw to neck to ear to shoulder to back to chest (not breasts) to stomach. Very romantic and sensual, I must say.

During the sex, he was unusually attentive to my needs and wants. He didn't want me to focus on his pleasure so much that he couldn't focus on mine. Afterwards, while have a drink of water, I get up and start getting dressed. He asks me to stay the night. So I do, despite knowing he has work early in the morning, and I had work in the afternoon. In bed, he ends up wanting to hold me or touch me (one hand touching mine while I was stretched out, with arms over my head, and the other hand on hip or stomach) without pulling me too close due to it being hot and both of us sweaty.

The next morning, he lets me sleep until the very last minute before he leaves for work, walks me out to my car, gives me a hug and kiss on the forehead, and then gets in his own car across the parking lot (townhouse parking lots).

It was a very unusual but awesome night, and my objective sources tell me that he may be wanting more than a just sex arrangement, that he may be coming around to a possible relationship.

Again, the next day, we don't really talk much, if at all. The day after that, we talked very little. Then the next night, his car gets broken into, and he's been very upset. I haven't heard from him since, and its been almost a week. I've sent him a few text messages here and there, but no reply. I don't really call people unless I know they aren't busy (I would send a text first asking if they were busy before I called). But nothing from him.

I understand its possible that he's still upset and angry about his car and stuff and may not want to snap on me about it unintentionally. I'm aware that he may be confused on what he wants with me, if anything. And its possible that the week before had made a serious impact on his phone bill that he may be cutting down usage on it (he has limited texts and minutes, I have unlimited and take full advantage of it).

I'm just not sure on how to proceed. I don't want to keep pestering him about what's going on. I'm not trying to pry into his personal life or anything he's not willing to share. But I need to know what's going on and if there's anything I can do to help.

What should I do?

View related questions: at work, best friend, bra , breasts, fiance, flirt, moved in, roommate, text

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A reader, anonymous, writes (8 October 2008):

This is verified as being by the original poster of the question

Update:

He actually sent me a text shortly after posting this. I had asked if he was doing anything that night and if he wasn't busy, if he wanted to hang out later. He replied back, "Nah, I'm not doing anything tonight." But that was it. It's been a week now and only heard from him once. He's home a lot because of his job, and only really goes out on weekends. I think a lot of it is still room mate conflict and tension (between his room mate and I) and he doesn't want to make things awkward because every time I've been over its been when the room mate isn't home or he is already asleep. But still no reason for him to practically ignore me :(

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A female reader, Ember13 United States +, writes (6 October 2008):

My advice is not to contact him for a week or 2. If he hasn't contacted you by then you can try again. It could be that he's really busy and/or confused dealing with car insurance and what exactly you 2 have.

On the other hand you could play up to some "emergency" and then he'd probably contact you. But I'd go with the first option. Sometimes people are busy.

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