1. "Can you use a male enhancement drug?"

In all of the commercials you see, it's a joint family decision for the man to use something extra to keep his yang up. But how does that come up? No pun intended. Does he decide it on his own and then mention it to his lady who then does internal jumping jacks? Or worse yet, how does a woman come to her man and say, "baby, you're really not cutting it in the hanglow department. I think it's time we discussed Extenze. Or Cialis. Or Niagra." It can't be fun.

Along similar lines...

2. "Baby, can you stop using your teeth, it's REALLY hurting my schlong!"

Women's ability to pleasure a man should be developed after, say, age 25 or 26. The cardinal rule of giving a Lewinsky is to not use teeth. But what if your girl thinks that she's great yet you always feel like she's treating your manbit as a chewtoy. It's akin to telling her she sucks at it (no pun intended) and that is one serious shot to her esteem. Most women get taught the finer points of schlonglove early in their 20's so they feel confident in their game after a certain point. And here you want to send her back to square one, you cad.

(But it's SUCH a necessary convo, by the way.)

3. "I'd like you to get a boob job."

With the alarming amount of foobs roaming the streets recklessly, I imagine that some were gifts and some were requests. But how do you tell a woman to throw some D's on that thing? It just seems rude. One should appreciate the boob, not plot for it's betterment. Then again as an avid, card carrying member of Men For the Upliftment (No Augmentation) of Boobs aka MFU(NA)B, I don't complain about life's little treasures...ya know, little or not.

4. "My parents hate you but I love you anyway."

I can't imagine being on the other end of that conversation seeing as how I'm adored by parents in 57 countries and Easter Island. But isn't that just awkward to bring up? It makes it difficult to plan holidays because who wants to spend time with people that hate them? I know I don't and wouldn't. There's only so much anxiety and discomfort one should have to suckup. No Ma'am. Word to Al Bundy.

5. "I love you, but I'm not in love with you."

Ouch. This has to be the most traumatic one of them all. It signals the end of the line. I'm not sure, as a man, how I'd feel about this if I had begun using Extenze for her. I compromised my manhood and you don't love me anymore. Then again, now I can take my show on the road. Ringling Brothers, b*tches.

Those are some awkard conversations to have. Got any more?