That's weird. It makes me think he's either interested in you or purposely trying to be obnxious. Let it slide for now. But next time he asks a personal question like that, give him a brief answer, then change the subject. If he keeps it up, jokingly ask him if he works for The National Enquirer. If he still persists, ignore his questions and talk about something else. I fianlly had to do that with my friend's husband. Once I quit taking the bait, he quit asking.

Hmm you gotta wonder about a guy who is so invasive...is he just not the type of person that is, as they say, self-aware? I dunno. I knew a guy who was like that and got the distinct impression that he was trying to get into people's heads partially because he felt he was better than everyone and liked to pick apart their lives and motivations as if he were analyzing a sample in a petri dish.

I would simply, and politely, say, "These questions are a little intrusive for me. I'm normally a more private person." Then change the subject. Or a simple "None of your business" with a sweet smile does wonders. Some people need to be told directly, and wont be able to take hints, so if you're simply hoping a wince or withdrawal from conversation will get the point across, dont count on it. Just be direct.

Woosification of america in full effect.

Tell the dude to mind his own business. say "is this 20 questions?" or my favorite "are you writing a book" if you dont answer him, he will stop asking.

stand up for yourself.

I'm with TrixieFire, simply tell him his comments are very invasive and you would appreciate him not asking personal questions. Tell him it comes off offensive and even condescending. I would also say your girlfriend needs to put him in his place.

I would never want to sit around getting questions like that shot at me. It would also seem that if he's not just arrogant maybe he's a little too interested in you? or maybe looking to set you up with one of his guy friends?

yeah, just stop answering him.

if you definitely DONT want to see him again, you could be honest to ur friend and tell her you'd rather it be u two (3's a crowd anyway)...you might lose a friend. These couples...man, sometimes they're like this **crossing fingers**

how obnoxious!

You know, this seems to happen to me all the time. Guys don't seem to get it why certain girls are single and the way they ask their questions it kind of makes me feel like its my fault when I know its not! I feel you on this on. Its a hard one but I agree Luisamapacha. Give vague, brief answers and change the usbject. Hopefully he'll get the hint and move on to get to know you in other ways. Good luck!

If he asks why you're still single tell him that the last guy you went on a date with wouldn't stop firing personal questions at you so you kicked him in the groin. He might get that hint...

My mother in law was like that when I first met her. It's tough to deal with, but you have to be very pointed about the fact that this guy is crossing the line. There's a difference between simple questions you ask when you first meet somebody (where did you grow up?) and intrusive questions designed to make one person feel in control (why do you see a therapist?). When he asks a question like that, tell him without apology that question is none of his business or is inappropriate and then change the subject.

One thing to consider is that this guy may be trying to isolate your best friend from her friends. Many abusers engage in behaviors that drive one's friends away...it's just a thought and something you might want to keep in mind as you deal with this situation.

Instead of just answering questions as they come, think of stories to talk about that would divert away from questions. Or start asking him a bunch to get to know him better. He might really be doing what your friend said, just trying to get to know you. He might have the best of intentions. If you do say something, I wouldn't do it in a confrontational tone. You can laugh it off... "geez, you're worse than my mother!" or something like that...

fascin8me nailed what I was thinking but couldnt articulate: he's asking questions designed to put himself in control. Be wary!

Either he's just a jerk and obnoxious or he is just socially inept. I, unfortunately, work with a ton of guys like this fiance you describe--most of them are socially inept and have absolutely no perspective taking skills and don't have a grasp on the idea that other people think differently than themselves. (e.g. He's not uncomfortable with people being invasive of him therefore he thinks why should they feel uncomfortable if he is invasive with them?)

I agree with previous posters--just talk to him if it comes up again. Luisa has a good tact--veer the conversation away and if that doesn't work make a joke of it.

And if all else fails, my old standby at bars/parties, when someone won't let up on asking stupid/insulting questions is to simply look around the room with a smile, acting like I am about to answer the question they posed, and say "Yeah, I'm just glad everyone is having a really good time." It totally flummoxes even the densest of people and it's a non-threatening way to move the conversation in a different direction without being obvious or causing any stress.

Good luck!

Be subtle when you talk to your friend about this. Find out his motivations and if he is that way with other people. Also let him know what boundaries you prefer. My best friend's husband is the same way but it isn't anything personal against me when he does it. He is a recruiter and is always in "command" and asking questions as part of his job. That is how he interacts with people because he doesn't turn that mode "off" when he leaves work. You can also do a little trick I do when I feel like having fun with it... I assault him just as bad with tedious questions.

Ok I'm going to be the devil's advocate here and take HIS side. Maybe he is interested in why you are single because he is thinking of the perfect person to set you up with. Asking questions like "Are you happy?" might mean he is keeping mental notes to take back to a friend. I would say you should confront your friend, not her fiance. IF you confront her fiance he might feel like you are attacking him or maybe he didn't realize what he was doing. Just politely tell your friend that you FEEL (key word) that her fiance is being a little bit intrusive. Maybe ask her if there is a reason and tell her that you would feel more comfortable if he wouldn't ask those types of things. I don't think she will be offended, I think she will probably just tell her fiance to settle down next time.

He's just a nosy guy. I've seen men like this and they think that just because their girlfriend or wife told them something about you, they should be able to question you. They seem to forget that you aren't originally their friend of many years. Just play it cool and answer a few of them...don't be pressured to answer all of them.

The guy has an issue with boundaries. It's time for you to put up a shield. The next time he asks invasive questions like that, reply ,"Why do you want to know?" Deliver it with a smile. Or say something like "I don't answer questions like that. I like to keep that info private." Again, deliver it with a smile. Access denied.

say "wow, all these questions make me feel like a celebrity!"
Hopefully he will realize he is being intrusive.If he keeps it up just tell him plain and simple that you like tokeep your personal life personal

mmm he sounds socially inept. unless he was a total jerk and wanted to frighten you away. but lets hope your friend has better taste then that.

This goes beyond getting to know you he is very intrusive. How does he know your in therapy? That too me is very private. You need to veer the conversation to another topic and start telling him that his questions are a little personal for you. There is also nothing wrong with telling your friend his questions are making you uncomfortble and they need to stop.

You need to tell your friend in full effect. You should also for one last time(as in you wont take his silliness)put things into perspective and turn things around on him.

UGH. Reminds me of one of my friends' husbands. He is the biggest jackass and will pick a fight over extremely personal things with any of her friends. He thinks it's funny. I personally think your friend should have stepped in and told him to back off, but I'm betting he's a controlling person-- am I right?

With this type of jerkoff, just tell him to his face that he needs to stop, he's making you uncomfortable. If he persists, and your friend doesn't step in, I would tell her privately that you're not going to be able to hang out with them again.

My hubby's brother can be quite invasive when he wants to. Usually I just laugh it off, joke around or just totally veer off from answering his questions.

It works pretty good, and if I felt that it's too invasive, I'd usually just let out a huge sigh, look away and just change the subject completely with a smile.

The worst he'd think of you is that you're a snob, but OH WELL. You're not his friend, you're his fiancee's friend and she knows you better than he does. But always be polite, because you don't want to burn any bridges (hopefully won't have to come to that point).

Good luck to you.

I notice in almost all the comments someone knows someone like that. Makes me think maybe he's just nervous? When I meet someone new I want to get along with I usually go on and on about REALLY personal stuff, sometimes my friends had to stop me from saying something really inappropriate. It's hard sometimes to socialize and maybe he is just being curious. Be honest and tell him next time you aren't comfortable with his questions.

"Are you writing a book about me?"
That's worked for me in the past!

I would ask him a question for every question he asks you. Give a little back. Either that or just tell him he's driving you insane and you didn't come over to be interrogated about your private life.

Not to mention, who the hell told him you were seeing a therapist? Did you tell him or is your girlfriend going and telling him all your business?

Yikes, that's a toughie. I would go with a raised eyebrow and an incredulous, "Why on earth would you need to know that?" to any questions he asks that are personal. I would also attempt to speak to your friend again, and tell her you absolutely don't want to be rude to her fiance, but that his questions make you REALLY uncomfortable, and could she possibly intercede?

This happened to me with my friend's fiancee. Meeting him for the first time, one of the first things he said to me was "I hear that you are in a crappy relationship." What?!?! Who says that? I was really offended and it completely affected my whole view of him and their relationship.

I know a few people like this. I think the intention is good but the effect is like being interregated by the police. Maybe next time you should say you prefer not to discuss these issues and change the subject to something a little lighter and less intimate.

I think this guy sounds socially awkward. It's hard not to feel cornered when you have 20 questions being fired at you but that's how some people are and you just need to deal with it.

I don't know how you are as a person, but when someone does that to me, i make a light joke out of it and say something like "Slow your roll there! Just let it be man..." (usually in a semi-hippie voice to make it sound chill and funny). And then i usually go into a story or ask someone around me a question to change the subject.

If that doesn't fit you, why not just say sweetly "Why do you ask?" when he asks something very intrusive. Or if he asks you that (stupid!) "Why are you single" question - just launch into a funny story or something. Good luck!

Nosey guy! Perhaps try again, and tell him to his face that his interrogation is making you uncomfortable, or maybe pull your friend aside and ask her to have a word with him in private, so as to not embarrass either of you in front of others (if in the setting of a dinner party or such). If nothing changes then maybe the two of you were just not meant to get along! DON'T stop seeing your friend, of course, but maybe avoid having too much contact time with her other half.