My boyfriend and I have been going out for a couple of months now. I'm heading off to college pretty soon but I'm especially worried about the condition of our relationship. See the hint is my boyfriend is really sweet but he has an immature side to him, where he will make inappropriate comments about eve the littlest things. Most of the time the comments he'll make are sexual jokes, and even though he finds them so funny they do actually make me quite uncomfortable. How do I tell him to stop or dial it down without coming off as a total preacher? Also he finds it funny to "pretend" to act like a jerk and will "pretend" to boss me around and say things to piss me off, however I know he doesn't mean it, it just irritates me all the same. What should I do?

With his personality, I would expect that no matter how you put it he will put up a show where he both "pretends" to be a jerk about it and is also really a jerk about it.

Sometimes people make inappropriate comments because they just miss the boat on the situation and don't realize their poor judgment.

Your boyfriend might "pretend" to be a jerk because it's an easy way to mask how he really feels, and can say something disparaging and call it a joke.

It's tough to have a "real" conversation with people like this sometimes since you don't know what they are really trying to communicate.

Sit him down. Tell him that you need to tell him a few things that are making you uncomfortable, and it is affecting the way you feel about him.

Then tell him.

Exactly what you said here. Give him examples. I wouldn't presume that he doesn't know exactly what he's doing. He likely doesn't repeat the same to his mother, teacher, banker or minister.

Maybe he is nervous, or shy, or as you suggest, immature. Maybe he is a jerk, and has been this way all his life and won't change, or can't change.

I would give him a chance, with first being totally honest about what you have said here. Just tell him. You will know soon enough whether he is the one for you, and worth more investment in developing a relationship.

Agreeing to what Jake2008 says, also, don't give in until he listens to you seriously. These kind of false prudence or bossy boys won't listen until you boss them / let them know that you are so serious which might even lead to a break up. Actually they are timid and afraid of losing you if they really love you.

How old is your boyfriend?

When you 'head off to college' will this become a long distance relationship? I ask because it may affect how much more energy you want to put into a very young relationship.

I do think you need to talk to him and explain how you feel about his jokes. Don't ask him to change for you, but because he sees there is line of good behavior he is crossing. If he tries to change for you, then you become the 'boss' and 'controlling' and possibly the target of more immature behavior whether you are there or not. It is not a good foundation for a relationship if one person feels like a parent and the other is acting out like a child.

Many times people don't realize how quickly their behavior crosses over into being 'too much' especially if they are playing around with friends. If this is the case with your boyfriend, you might see if the two of you can come up with a signal for you to give him when he is getting out of hand.

If you feel like you are getting frustrated and upset with him and talking hasn't changed anything, walk away. Part of dating is finding out if the person has traits you like and those you don't. If the negative traits outweigh the positive, it is time to accept the person isn't a good match for you.

Good luck.

Or he is a jerk and perhaps you should consider a new boyfriend