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Should I wait, or should I make the first move?

Tagged as: Big Questions, Dating, Online dating<< Previous question   Next question >>
Question - (1 March 2010) 1 Answers - (Newest, 3 March 2010)
A female United States age 36-40, anonymous writes:

I apologize for the length ahead of time as I know this may come out a bit longwinded.

I met "J" online. He actually got in touch me with via a popular social networking site (not a dating site). We're both from the same area, and have mutual friends. It turned out that we even went to high school together (although he graduated a few years before me). I did not recognize him from high school, but from a mutual friend.

I didn't know his name, and it was years ago, after he had graduated. But once I mentioned the mutual friend's name (to see if this was the same guy), he immediately remembered how I recognized him (our mutual friend was his 'boss', he was a mechanic, and his boss had painted my car an outrageous color). He asked if I was the one who drove that car - he didn't equate me with that car when he first initiated contact.

So he is local, but works a job that requires him to travel extensively. Most of the time, he's only home for a few days out of the month. We had exchanged numbers days after the initial contact, and hung out at my place when he was in town. It was then that he told me that he remembered me from high school, despite our class gap; he was a senior when I was a freshman. He remembers just about every time he's seen me with his boss/my friend (usually about my car). I find this to be a bit interesting...

Earlier this month, after about 6 weeks of really knowing him, things go towards a more sexual attitude. We had been discussing the topic quite frequently, and making very direct and forward comments and innuendo. He was out of town for work, as usual, but he called/texted daily. He sends pictures he takes from his various locations - on the road, hotel rooms, attractions, etc. One day, he mentions an "ongoing medical issue" and just wasn't in the mood for our usual sexual flirting, but it didn't dampen our spirits.

Still, this wasn't a relationship thing. I was attracted to him, he was at least interested in some degree, but nothing had been discussed about dating. It was discussed that he could crash at my place as he's been having problems with the coworker he normally stays with/travels with.

He drove 13 hours the night before Valentine's Day after a full day of industrial work, and arrived at my house the morning of. Did not sleep him, and he didn't make a move to. It was just nice cuddling and sleeping. Total clingball in the bed though, he is. But I loved it.

He hasn't left for a long period of time as his current assignments are fairly local day jobs, so we've been spending a lot of nights together. A few days ago, he tells me reluctantly (and on his own) exactly what the medical issue is, and that he's self conscious about it because it is near his genitals (I won't go into detail about it, but its not an STD or anything like that), so its hard for him to get in the mood when it recurs (its an occasional recurrence).

Okay, cool, I get that. I understand his self consciousness. I'm fine with it, and impressed that he had the guts to tell me about it. Shows me that he's starting to trust me... I think.

It kinda makes me weary about making the first move though, since he hasn't even gone in to kiss me. My gut tells me that he's still put off by his own self consciousness. I don't want him to reject my advances since I know not to pressure him for sex while he's dealing with his issue. But I would like some sort of physical reassurance that he's interested in me in more than just a friend way, other than the cuddling in bed.

So here my actual questions:

1. There are other "signs" that show me he is interested in me beyond that of a friend - he randomly picks me up from work, he pays when we get delivery, he drove 13 hours on zilch sleep to be with me on Valentine's Day (and night after I got home from work). He will call me all randomly for what appears to be no reason at all. We've made some concrete plans (but without concrete dates) for an upcoming movie, and a trip to the zoo when it gets warmer. Still, I ask myself if he's REALLY interested. Am I reading too much into these "signs"?

2. There are other "signs" that tell me that he's just not that into me. Just recently we had discussed going to the aquarium, and told me he'd get up with me soon about it (as it was arranged for that same day). He ended up having spur of the moment plans with his friends, and even said that the aquarium was a long drive yet it was his idea in the first place. His new plans with his friends resulted in me wasting my day off as I only saw him that morning before he left.

He hasn't tried to kiss me, and from what I gather, he's fairly aggressive. He has no problems or hesitation to cuddle me or tickle me after finding out that I am deathly ticklish, and I am understanding of his reservation of sexual activities. But kissing? Making out? Why hasn't he has made the "first move" yet?

3. Stemming from #1 and #2, would it be wise for me to make the first move? To just in and kiss him? I'm not afraid to as I'm confident with doing so in the past, but if he's really not that into me and just using me for a place to crash and a warm body next to him. I like cuddling, but if he only just wants to cuddle, he can get a puppy.

View related questions: co-worker, exchanged numbers, flirt, in the mood, kissing, period, std

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A female reader, anonymous, writes (3 March 2010):

I think it would be a very good start. But after the initial start he should be the one to start the next time. This way you can tell for sure if you are wasting too much time with him. The kiss will help you know for sure what his true intentions are. If he pulls away you have a problem. Best of luck and remember that if he just is not that into you, you need to move on. You deserve it!

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