Ask a Dude: What's With the Cryptic Texts?

Dear Dude, 
Get ready for a toughy—the way this guy has demonstrated interest in me is far beyond my comprehension. He started flirting with me in October: sitting next to me in class, texting me nonstop, asking if I had a boyfriend, etc. I was very receptive and flirtatious back, but nothing happened. Physically speaking, the most we ever did was hug one another. We haven’t done anything more than study alone together several times in his dorm room—again, nothing physical. Out of the blue, he has told me that he has a lot of respect for me and that he thinks I’m intelligent, and he has mentioned my various accomplishments to his friends. You think everything would be good and that he’s just a little timid, but here’s the tricky part:
Sometimes when he texts me, they’re very direct and sexual.
Earlier on, he has asked me how far I’ve been even though he knows I’ve never had a boyfriend before and that I take my morals very seriously (although, I’m not entirely against having premarital sex—I just want to make sure I am in a committed relationship before doing so). At the very beginning of second semester, we were joking around via text that we were cold and that we should warm up together. When I asked him if this was an invitation to snuggle and have a movie night, he said he only cared to snuggle without pants on. I got really upset by this when he continuously pursued the topic, asking me what I was afraid of and telling me that trying new things could be fun, even though I told him I wasn’t comfortable with that by any means. He did apologize for the behavior and things were just as normal as they always were when we saw one another in class a few days later.
Then about a week ago, he has asked on several occasions late at night for me to come over for what he phrases as being a “pajama party.” I responded that I would like to hang out with him so long as it wasn’t in obscure hours of the night, but we haven’t actually set anything up. I’m severely frustrated by the whole situation, and my friends have mixed feelings about him, some professing that he’s toying with me and others saying that I’m paranoid for thinking that he’s using me for sex.
What is he exactly after? I think I have made myself perfectly clear on my unwillingness to casually hook up, so if he is trying to just hook up with me, why does he continuously pursue it when this has dragged on for months and his tactics aren’t working?
I really don’t know what do anymore. Everyone refers to him as the prototypical nice guy, so I don’t know why this keeps happening to me. It just kills me, and at the risk of sounding cliché, I never cared so much about a guy before, and I’m not willing to give up just yet, which probably makes me sound certifiably insane. At the very least, if something doesn’t develop between us, I don’t want to make this more awkward than it already is.
Help Me,
Victim of Sexual Cryptic Texter
Dear Victim of Sexual Cryptic Texter,
What does he want? SEX. When does he want it? NOW. What does he want? SEX! When will he get it? Well, that’s your call, isn’t it?
Based on the evidence you’ve given, I’d say he may not just be looking for a booty call but he also might not be looking for a heavy duty relationship. He could desire the ever popular FWB. The fact that the two of you have been tap dancing for months on end is some indication that he’s not only looking for the quick fix. On the other hand, some fellas love a challenge and who’s to say that, in his mind, you’re not his best option for a little hanky panky?
Texting and e-mail is the perfect outlet for the inner freak. You can claim to save a little face because your horniness isn’t coming out of your mother. However, every nice guy has a sexual deviant inside him somewhere. We get horny. But we’re scared we’ll come off creepy and get rejected. Somehow, using an indirect way to directly let our doggedness is less…real. Does that make sense? I’m not claiming it does. I’m just saying it happens.
So, what’s my advice? Confront the sombitch! You set him straight and set it right. Situations like this all come down to setting the boundaries. You’ve clearly set one boundary: no naked cuddling! He tested it, when you got mad, he backed off for a time and now he’s testing it again. Remind you of something? Like, a 2 year-old?
You say that you’ve never cared so much about a guy before. Then, here’s my question to you: Why are you still just friends? What’s preventing you from giving him a chance to be more than friends? I’m not talking about having sex; I’m talking about trying to have a romantic relationship. You don’t suddenly go from friendship to marriage; there’re a few steps in between but the two of you haven’t taken any of them from the sound of it. If it’s the fact he’s pushing so hard and you can’t get past that, then you’ve got your answer already: let the dog go.
However, if you still want him to be a friend then you need to make it clear. If there’s truly no chance of the two of you changing that dynamic then make sure you shut the door on his little guy. However, if you think you’d like to go down that road then sit his ass down and lay out the dealbreakers. Tell him what you’re comfortable doing and not doing. Tell him that the pace is going to have to be this slow, or this fast, and if you want to switch up gears then you’ll do it when you are ready.
You don’t have to throw the baby out with the bathwater yet; it all depends on if you want the baby in the first place. Make your choice: do you take this to another level, and make it clear what that level will and will not contain, or do you say “enough”?
Start with what you need – other than to not have sex – I’m speaking more on the emotional plane. When that’s clear, everything else will follow.
Taking a cold shower,
The Dude
[He’s good, right? Sigh, we know. Check out The Dude’s other insights into the male mind right here.]

Sex in the News: Women Love the Uncertainty
Sex in the News: Women Love the Uncertainty
  • 10614935101348454