A semi-complicated friendship.

I have a strange relationship with two of my really good friends. You see, I've known one since grade school, lets call him Matt. He happened to have married my other good friend who I had met during high school, lets call her Cassie. Not too strange so far, but since their marriage things between the three of us have become a little stressed/strained.

You see, I'm always joking around but when my jokes are directed to my female friends it is immediately considered flirting, which I feel is really ridiculous. Now Cassie and I have always joked since our freshman year in high school, usually in the form of insulting one another playfully. Well, apparently since I joke around with lines like "You're always a sip of gin away from giving lapdances" (weak line, but when you're texting one another who cares?), it drives Matt ballistic and he demands I stop all contact with his wife.

Now, if I hadn't known Matt my entire life I might be able to understand his concern as the overprotective husband but we grew up together and have no bad blood between us. I feel torn because I've known Cassie long enough to consider her a really close friend. Needless to say, I feel it's a bit drastic and unjust of him to make such demands. I've talked to Cassie asking if our conversations have caused any problems but she assures me it's nothing. In fact, apparently I'm an isolated incident as Matt has no problems with Cassie having contact her other friends, guys included. This adds to my confusion and frustration.

Anyway, I was hoping to get another set of eyes and opinions on this subject. Am I really in the wrong? Even if I stop my lame ass jokes, I don't think stopping all communication with a good friend is fair. I've tried to talk to him about it, but Matt refuses to listen and just tells me to stop texting his wife though he has no problems with us hanging out. I'm hoping to get this all sorted out before it snowballs into some ridiculous teen-like drama and all advice, observations, and other such remarks are appreciated.

Well, she married the guy. Some guys are just like that. I have a friend who I know that if I said something like that to his girlfriend, he'd probably hit me in the face next chance he got, and I also have friends who would think it was hilarious and encourage it. But when it comes down to it, you have to respect his boundaries or you will probably lose both of their friendship. It isn't that hard to watch what you say, and I'll be honest, I don't know how comfortable I'd be with my significant other texting another straight guy and flirting like that. Anyways, you're probably going to have to stop it, it makes your friend (matt) uncomfortable, and if he really is your friend, you should respect that it makes him uncomfortable, and stop flirting with her. Not to say you should cut off contact with her, just watch what you say to her, she is married and some things are not appropriate.

The guy is completely in the wrong. Completely. Ask her what she wants you to do.

It's Matts problem, not yours. You're not flirting, you're just being friendly like you were before they got married, nothings changed. You're good friends with both of them.

If I were you I'd go and talk to him, make him understand there's nothing going on, its just jokes, like it was in high school.
If he fails to see this, tell him it's his problem.

I'll be the first to say that you're the one being unreasonable here. Surely you're whole entire relationship with Cassie isn't based on just insults and terrible jokes; and it's one thing to say this to her face to face but to actually text her messages with sexual innuendos, I mean yeah your friend Matt is going to get mad. I'm willing to bet that he isn't jealous or afraid that you're trying to "hit" on his wife, but that you're being disrespectful to her and it bothers him even more since it is coming form you (a longtime friend). Look at it from that point of view.

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Originally Posted by Absolution

I'll be the first to say that you're the one being unreasonable here. Surely you're whole entire relationship with Cassie isn't based on just insults and terrible jokes; and it's one thing to say this to her face to face but to actually text her messages with sexual innuendos, I mean yeah your friend Matt is going to get mad. I'm willing to bet that he isn't jealous or afraid that you're trying to "hit" on his wife, but that you're being disrespectful to her and it bothers him even more since it is coming form you (a longtime friend). Look at it from that point of view.

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That's crazy. He's known Matt all his life and whatever dynamic he's had with Cassie he's had for a long time.

I have two friends who are married now, Matt and Tasha, since I've known Tasha(about 3 years) I've always hit on her, playfully. Matt and I(friends for 5) have always been pretty ruthless when talking about women, whether it's saying how hot/ugly they are etc. Tasha doesn't get pissed when Matt playfully hits on my girlfriend, and Matt doesn't get pissed when I blatantly hit on Tasha(and Matt knows I wouldn't mind screwing her, as I've expressed my interest since I've known her). So in the same shoes as you, and with less friendship experience that you have between the two, If I were in your shoes I'd tell Matt that it doesn't mean anything and to get over it.

Then again I'll talk mad shit to friends, whether it's meant or just playing around, and never have problem.

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Originally Posted by Vengeful Scars

Then again I'll talk mad shit to friends, whether it's meant or just playing around, and never have problem.

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That's how it is with all of my friends, regardless of gender, age or creed. Matt and I have had hour long pissing contests where we just talk shit back and forth. The same goes for me and Cassie, but admittedly she has a quicker wit and a damn sharp tongue and usually carves me up pretty good, which is all good fun as well. I still mudsling with Matt, but as soon as Cassie and I start throwing puns back and forth he gets insanely defensive.

Honest to God, I don't know why he'd consider it flirting and if he does, why in the hell he'd be jealous/or upset. Lord can attest (as well as Captain Castle) that unless I have a fucking bottle of chloroform on hand I'm not seducing anyone. Sounds like your friend Matt is a pretty chill guy, which I used to think about my buddy.

I am an unprofessional unlicensed self-proclaimed Casidual Discourse psychologist and therapist. This is my assessment of the situation.

Cassie probably had a crush on you for the longest time and she told Matt who is worried that you would, even if inadvertedly, steal her away from him. You also like Cassie because male and females cannot have completely plutonic relationships. Probably should determine how much of a douche bag asshole your so called friend Matt has been to you your entire life, focus on all those negative memories, and pursue and claim Cassie for yourself. Marrying her would only be an option.