Breaking the dating/relationship barrier (like sound...)

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So, I met this absolutely wonderful guy online and we sent each other something on the order of 15 1K-word messages before we finally met. When we met, I went to his campus and we spent all night together (doing active things with his friends and talking alone). We had some more phone calls and messages, and a week later, he came to visit me...and stayed o'ernight and there was cuddling and making out. During the process, he, very tactfully, resisted my sexual advances. Which is fine, as, in hindsight, sex would've been and will, in the future, be...difficult...for reasons I'd rather not go into.

We spent about 20 hours together on the first date/meeting, and about 30 hours together on the second one. In addition, when he came over to my place, we fell asleep in each others' arms (showing large amount of trust for each other, I think).

I date people quite often, but it rarely gets anywhere past the second date. This is an exception and I think that I might well be in love. Bugger that. Make that MADLY in love. Although I normally abhor doing things on/for holidays, I want to give him a large (creatively-fueled) gesture of love/passion/whatever on V-day in the hope that we can break the dating/relationship barrier.

Facts:

1. We met for two dates which lasted a total of ~50 hours of together time.
2. There was intimacy.
3. I plan on making his V-day beyond awesome.

Notes:

1. We live ~2-2.5 hours away from each other. 4-5 hours round-trip.
2. We both have lots of things to do.
3. Transportation is expensive.
4. I can't imagine being able to afford seeing him more than once every week or two. Both in terms of time and monies.

Slightly unrelated questions:

1. Should I apologize for the sexual advances? If so, calling would be best, right? Also, if so, should I have done so immediately?
2. Given that we're, still, only dating, is it wrong to ask him to clear his V-day for me, oh, say, two weeks ahead of time?

Queries:

1. Despite the dates being REALLY long and intimate, is the third/fourth date too early to ask him to commit to a relationship?
2. How do I ask for that level-up in relationship status without being unnecessarily awkward? Like most of you, I'm EXCELLENT at being unnecessarily awkward.
3. Withstanding having sex, which, although my genitalia desire very much, I'd rather not pursue just yet, how do I know the relationship status has (or hasn't) leveled up?
4. Any other suggestions on breaking the dating/relationship barrier?

Last edited by Aerith on 30 Jan 2012, 3:19 am, edited 1 time in total.

I wouldn't apologise for the sexual advances unless you think he felt offended by them. However, I would refrain from them in the future, as repeating them might start to annoy him.

I don't think asking him to clear valentines day is unreasonable or creepy.

Erm, great. Thanks. I thought as much. Just being careful. I highly doubt he was offended.

Any opinions on the main questions at hand?

1. I have no clue. It varies from person to person how early they will commit.

2. Also no clue. I always screw things up at that stage

3. Hmm... maybe an exchange of I love you's or some such?

4. Don't give yourself time to over-analyse.

There could be a number of possibilities as to why, from one perspective, I think you should back off and let him pursue you, if he likes you enough, he will pursue you and if he doesn't, you know he doesn't like you. If you insist, you could run the risk of being second best or being dumped for someone that is more of a challenge to him. If he has been hurt in the past, he may afraid to jump right into a committed relationship with someone.

From another perspective, he could be shy and not used to being assertive or taking the initiative so showing him that you like him could lead to a relationship once he has the green light or he may see you as easy and simply use for sex since he can get the milk without buying the cow.

"I think you should back off and let him pursue you, if he likes you enough, he will pursue you and if he doesn't, you know he doesn't like you."
I agree with Wolfheart on this point.

"simply use for sex since he can get the milk without buying the cow."
On this point...if he feels this way, he's a shmuck you are better off without.

I wouldn't even talk about the sexual advance. leave that to him for now. he might want to show you he wants this to be something special. Boys will do this to show you respect. accept it and go along with his timetable.

As for Valentine's Day. I don't want to burst your bubble, but he is aware of it and I am positive he has thoughts on it. DO NOT go overboard. Let him take the lead as hard as this must be for you. In order for him to feel like he is invested in a relationship, he needs to be given the opportunity to do so. Care about him enough to let him do what he feels is right for the both of you. Keep it light and fun. THIS is what will keep him with you.

Thanks, but, to be honest, I feel that he's SO AWESOME that I wouldn't mind being second-best nor being dumped for someone that is more of a challenge. I have a strong tendency to not pursue friendships/relationships with people only to, three months later, wish that I had pursued them. I'm not willing to pass this one by. Aside from that, both of these are quite unlikely, as his previous relationship (ending ~4 months ago) was with someone very similar to myself in age and background.

The second perspective is far more likely. He IS rather shy. He, like myself, is fundamentally unable to engage in casual sex.

The problem is in achieving the green light and knowing what in bloody hell it looks like so that I don't miss it.