ummmm i think u should just see who u wanna see and well kenny will come to be fine....he needs some time 

Wow this is Dr. Phil tough. I suppose it comes down to a few options.

A. You keep the friend "Kenny" and lose out on what could be something really good, "Ryan".
B. You keep what could be something really good, "Ryan" and lose a friend "Kenny"
C. You see "Ryan" on the side and agree never to meet anywhere "Kenny" could be, in order to avoid the conflict (Best of both worlds if I may)
D. You sit down with "Kenny" AND "Ryan" at the same time and get things sorted...

But personally, allowing "Kenny" to be a wet blanket in your life hardly seems fair.

Here is my example, I have a really good friend, a couple of my other friends and I don't particularly like his girlfriend sometimes... She's a control freak, hardcore. She's VERY fun and we like her as a friend, but sometimes she annoys the shit out of us and pulls strings to have our friend forfeit his balls and ditches his guy-friends. However, we cope, we sometimes bitch and complain to each other, but we leave them alone, because they seem happy together and that is worth more than possibly ruining not only their relationship but our friendships.

Moral of my story, do what makes YOU happy and worry about other's feelings as it goes. Because if you are unhappy but your friends are, how is that healthy in the long run? There will always be resentment somewhere.

Basically, in that situation you have to choose between the two. Because by dating Ryan your hurting Kenny. Doesnt matter whether or not Kenny has the right to stop you to, hes still going to be hurt. I think he just doesnt want to be the one to stop you, he wants to know that it was your decision alone, that made you not want to date Ryan. He wants to know that it was in your heart to be closer to Kenny by not being with Ryan. But on top of all that, as mean as this sounds, I think you need to get rid of Kenny, or date someone that isnt Ryan, just to make it clear to Kenny that he needs to go get his own life. I dont think its healthy for him, knowing he really likes you, to stick around like that, I think since you gave him a bit of hope by making out with him, that hes going to stick around in case you change your mind. I doubt you plan on coming around and dating Kenny. 

of course they'll always panick.

it's awkward.

I think you should have the choice of dating whomever you want, but not in this case. Ryan, as you have mentioned, is one of Kenny's best friends and housemate. If you continue to see Ryan, you'll not only hurt Kenny, but will cause tension inside an environment where they both call home and possibly jeopardize their friendship. But I think you know all of this already that's why you decided to stop seeing Ryan.

There are other men out there and they are just as independent and strong as Ryan. It simply isn't worth it. You're not in love with Ryan so just let it go. Be the bigger person and let Kenny have his way. He's still got a lot of growing up to do and you don't want to be in a situation where you'll come out as the bad guy.  

This may sound like I'm attacking you but I'm not so bear with me:
I think you took the easy way out by breaking up with Ryan with the excuse of Kenny's discomfort. Didn't you think about that when you first felt you had to ask his permission in the first place? And knowing Kenny, didn't you know he was going to be weird about it longer than most people would since you two have attempted something more? And so instead of working it out with Kenny; having a talk about how important it is that he's still part of your life and treat him like a man rather than "made out of porcelain", you just thought  it's just easier if you broke it up with Ryan. Didn't you feel that maybe Kenny would have felt humiliated when you told him? That you're treating him like a boy, a baby, anything other than a "strong" man that you seem to admire?
I think as much as Kenny has been duplicit in his actions (own up to what has been said: since he did say you should date Ryan, why is he acting like it's not? if he felt this way, he should have talked to you about it in the first place) you too have been selfish. They're housemates and best friends; no  matter how "okay" Kenny said he was, it was a pretty big thing for him to accept. He couldn't have just embraced you two and say "go for it" ask details of your happiness and whatever. he's obviously a sensitive person who's still somewhat emotionally immature and dependent on women who are stronger (you) so in knowing him and his reactions, you still went for it. You took that risk and just when it gets hard in dealing with K, you took the easiest way out. It may not seem like your fault but you prob. made Kenny feel like the biggest pansy/baby/weakling because you broke it off with a really good guy FOR him.

I also think perhaps Kenny is not the problem to why you've concluded to end with Ryan. Maybe you two were feeling "off" and assumed that was the thing with Kenny. You two must have thought about the whiplash effect to your relationship before you went through it, right? Anyways, if Kenny is a good friend as you keep saying then I don't think you would have went out with Ryan. Guys have that code thing: "bros before girls" thing?  Plus I don't think you should give into Kenny's whims anymore. He can't live in a protective bubble forever, he wants to be treated not like he's made out of glass, so stop indulging him! :) Because you're a woman of strength he depends on you and since you're the one that "got away" he's always going to have a soft spot for you, eh?
don't date friends of friends that liked you. shit, don't date best friends of friends that liked you. it's complicated for no good reason.

Guy wants to act like a gentle but he is overwhelmed by his emotion issue. Even you guys have not been really dating but obviously he sees you as a girlfriend and how could it possible to see his "ex-" gf dating another man?

That's not a question about "right" or "wrong", the situation means to hurt Kenny and he needs to learn from it.

Kenny, as the "nice" guy, has probably gotten passed over for his friends countless times in the past. To have that happen by a girl he really likes is probably really frustrating.

It sounds like a difficult situation all the way around. Kenny, in his heart, can't stand the thought of you dating his friend. But in his mind, he would never want to stand in the way of your happiness - or his friend's.

You're going to have to choose: your friendship or your relationship.

It may not be "wrong" for you to see Ryan.. But yeah. He really doesn't want to be that guy. He may feel like it's inadvertantly him hurting the two people he cares the most about, you know? Two of his closest friends. He really likes you, though. So, to keep from having to face the fact that the girl he liked ended up with his best friend, he just saw it best to avoid you.. You know? When people don't know how to deal with problems, they typically try to avoid them. Right? So, yeah.. If you and Ryan date, know that for a good while, it may make things very awkward, especially with Ryan and Kenny living together. So, perhaps put of seeing each other until one of them moves out, or something? You know? That way it won't rub it in his face, so-to-speak, as much anymore. Maybe that would help.

As I said, while it may not be "wrong", so to speak.. It may also not be very considerate. You know? So, if you want to be considerate, talk with Ryan about it, and see if he'd be willing to wait a little while on the dating thing. I don't know what else to say specifically right now. Need any more tips, let me know. I'll try my best to help you!

<3, ~*Akarui Mitsukai*~

kenny should have said he was uncomfortable with you dating his housemate. but he didn't and him being passive-aggressive is making it worse.

i don't think you should stop yourself from seeing what could happen with ryan, despite the friendship with kenny. if kenny was a true friend, he would swallow it and be happy for you. sounds like he kept such good relations with you because he thought you would eventually come around.

I think you should see Ryan again. Kenny can choose whether he wants to be a supportive friend. You obviously are, but I don't see his loyalty to you.

Did you not read what you wrote?

"We asked Kenny if it was okay if we started seeing each other. Kenny
said we should go for it, as long as he didn't have to see it or hear
about it."

Of course he will avoid you! He said it already.. he doesn't want to hear or see it. You can date Ryan...but spare him. Did you go around his flat parading your relationship? He wants to be a good friend by letting you date. Maybe he also knows that he is in no position to tell you to not date that's why he said yes. But that doesn't change the fact that he still has feelings for you. He's hurt. He can't control it.

I kinda get what Kenny was feeling when (if) you told him he was the cause of your breakup. It's like a double whammy. Now you're telling him he's a pansy too... cause you had to break up cause he cant handle it...putting the blame on him. Nobody wants to be "that guy." And trying to set him up with other people might make him feel like you pity him... cause he can't find girls on his own so you're like, "Here! I'll find one for you so you wouldn't be a crybaby if I do your bestfriend." I guess...just give it time. You said he has woman issues so he has to fix that himself.

This is a no win situation.