No, you are absolutely NOT blowing anything out of proportion. Your "gentleman" friend is a fucking asshole. Anyone who calls you a whore is a fucking asshole. He's not worth your time, whatever his redeeming qualities. DTMFA. Get rid of him and cut him out of your life. You shouldn't have to put up with insults from ANYONE and a man who does this is NOT your friend.

I agree with Dominique, though if you don't want to DTMFA, I would recommend talking to him in a calm, mature manner about what he does and how it hurts you. He may laugh it off at first, but that's probably because his pride will be hurt. It's hard to have someone telling you calmly and logically that you're hurting their feelings, but I can guarantee it will make him think about it. He probably doesn't know he's doing it. I had this experience with many male friends when I was in high school in college, and I laughed along with them and wanted to believe that they were really good people. He might be, but you do need to bring it up. If he doesn't change at all after that, then it's a pretty good indication that his "gentlemanly" ways are a bit of a facade.

It is absolutely something you should bring up with him. Like Dominique said, you are NOT blowing anything out of proportion. It's jokes like these that perpetuate damaging gender stereotypes and a sense of patriarchy. I know it is difficult to approach friends who say hurtful things, but if he is truly a friend he should want to know that the things he says are not only hurtful and demeaning but embarrassing for you. I think if you open up to him and demonstrate that the term "whore" is a gender-specific term that degrades women, perhaps he will change his ways. But...he might not. It that's the case, I recommend you keep trying to show him how it is hurtful. This friend is obviously in need of someone like you to teach them a few basics of feminism. However, if it doesn't work after a while, get tough with him, or leave him. You shouldn't put up with someone who likes jokes that not only hurt you, but all of woman-kind.

The first part of this problem starts with you: laughing along with someone who is saying hurtful things to you (that would be considered hurtful by most any woman) is no better than being an insensitive or mean jerk that makes such remarks. I know you don’t mean to, but when you ‘go along with it’ you are giving him the green light to continue speaking that way. It’s a strong nonverbal signal that what he is doing doesn’t bother you. So how can you get upset with him for continuing to do something that he has no idea bothers you at all? It’s time for you to learn to be assertive without worrying about losing the approval of the person who is treating you poorly. I’m always curious when I hear people say, “He’s really a great guy at all when he’s not_____________(fill in the blank: hitting me, cheating on me, calling me names, getting drunk and blowing all the rent money). It makes me wonder sometimes what someone has to do to be considered a bad guy. We will never get rid of all the jerks in the world but we can all try to give them one less safe place to be one.

i can't tell you how many times i've tried to let things like this go, because i kept telling myself someone is a "nice guy" or a "nice girl". because frankly, how they are acting is NOT NICE. and you deserve to stick up for yourself, and you don't have to excuse or pardon their behavior if they are doing something like what you stated that is hurting you. eff that.

Why is this "gentleman" calling you a "whore" yet teasing you for being so innocent about sex? I can't imagine that this person is as decent as you say he is, but you have a definite opportunity to step up and open dialogue about how often cliche language is hurtful to you personally and women in general. If he is a nice guy (as you believe), he'll be interested in trying to understand. Being upfront about your feelings is not uptight, and if he makes you feel that way then he is not a good friend. When I talk to people about their use of oppressive language, I explain why it's hurtful to me and always encourage them to call me out if I'm using language that they find offensive.

This is something I struggled a lot with when I was younger: trying to figure out why I didn't like the things my friends were doing and saying.

I discovered that they weren't really my friends, they were just people who I was hanging around with.

Let me put it this way. What things make a person a friend? Is it just someone you talk to and hang out with or is it someone you can turn to with your honest opinions, hopes, fears, and dreams? Is it a person who will talk down to you or a person who will alternatively challenge and support you so that you can be your best?

If you can't be open and honest with a person, that person is not your friend. It may be that when you open up to this "gentleman" friend of yours, he will see the error of his ways and do his best to change. If so, he was a real friend to begin with.

But I have a feeling that the reason you're afraid to go to him with this is because you'll realize he's actually a dick and not really your friend at all. So you have to ask yourself, are you okay hanging around and sharing your time and life with people who aren't real friends? If not, you have to confront him. If so, I guess I just feel really sad for you.

Forward this post to him. If he doesn't get that you wrote the post and that the person you're talking about is him, tell him.

Hmm, I don't really have enough information...is this guy just a friend, or a romantic interest? Does he call you a whore "ironically", because you are actually innocent? In that case, he may just be making a bad "joke" and thinking he's being funny (he's not ;) ).
You say he's "nice", but don't say how he is nice. What are his good qualities? And, how old are you? I may be assuming, but you sound young.
In my younger, less confident days, I often had the friends who would relentlessly rip on me. They'd fling burning insults, but then say they were "just kidding". Being shy and wanting to be liked, I took it.
As I got older, I realized that sometimes, when they say they are "kidding", they really aren't.
Now, I have a wicked sense of humor. There are friends that I have who call me dirty names, like "fucker", and I do it right back. But, it's understood between us that it's okay. I don't do this with just anyone, and I would be mortified to learn that I'd hurt someone's feelings. I'd apologize, never do it again. This is different than the "insult! just kidding" friend. They will get defensive and accuse you of having no sense of humor. Really, they just want a doormat friend they can lord it over.
If he is this friend, I agree with the other posters: get rid of him. But if he is just a terribly misguided friend (you'll know which one he is by his reaction to your hurt feelings), talk to him and give him another chance.

Confront him politely and explain he makes you feel uncomfortable, and to please stop. If he's actually a nice guy and your friend, he'll stop. If not, DTMFA.

As someone noted, it may be his way of trying to treat you like "one of the guys," and he doesn't realize he's actually bothering you.

Maybe I'm just old and ornery, but this guy is not your friend or a "good guy" if he can't or won't pick up your discomfort cues, and it's not your responsibility to educate every insensitive misogynist. You sound like a lovely young woman, and surely there are plenty of worthwhile people who would love to be your friend!

No, are you ready? Because I have the BEST ADVICE EVER. (I'm so excited.) It has always worked for me.

The next time he makes a crude joke or calls you a name, just look him in the eye (not glaring) and shrug.

He expects you to engage him - to either start throwing back jokes (which gives him the impression that you find it acceptable to some degree) or to "play the crybaby" (which he'll see as weakness to exploit - not my opinion, it's just how he's likely to see it). He's so used to treating other people like this and them either being amused or insulted, that by not-reacting (but not ignoring) you will completely throw him off. He probably won't stop, at least not right away, but you will see that he stops targeting you especially.

He wants people to play his game. You're not blowing things out of proportion, but I honestly doubt that confronting him will help at all. In fact, I think it'd just make it worse.

You're not detailed enough for me to say whether he's an asshole or just a little tone deaf. Most of my friends make a lot of sex jokes, and I have to keep myself in check when I'm around friends who aren't okay with that.

If always pretend you think it's funny, he probably doesn't even realize that you're bothered. And if he really is a nice guy, he'll stop if you ask him to.

If he doesn't stop you're justified in kicking him to the curb.

I DID confront him today and he felt truly sorry about it and we made sure he'd never do it again.

Then, well, I guess you did the right thing.

As some other commenters have remarked, if you pretend that you think it's funny, he'll assume that you really do think it's funny and keep on doing it. As far as I can tell, it's generally best to be honest and open about this sort of thing, so you can nip it in the bud immediately and not let it get to the point where it becomes a problem.