Questions You Never Want Your Boyfriend To Ask You

Questions You Never Want Your Boyfriend to Ask You

I am not a fan of confrontation. While most girls want to have long, exhaustive conversations about their feelings and relationships and the color of the sky, I completely avoid such chats at all costs. I am perfectly content to float along, never having “the talk” to define whatever it is me and my current man friend are doing, or spend hours discussing for a theoretical future involving a wedding dress and a white picket fence while he looks for the nearest sharp object to put himself out of his misery.

Therefore, the second the tone of a sentence turns to questioning, a pit forms in my stomach – particularly if the inquiry is coming from my boyfriend/friend with benefits/random dude. What if I say the wrong thing? What if I offend him by accident? What if I fuck up this thing that I’m not even entirely sure is an actual relationship? And while really any question makes me nervous, there are some in particular that can send me into a complete tizzy.

“Did You Finish?”

If he has ask, the answer is no. Always no. But assuming he is the unicorn of guys that actually cares, this question brings up quite the conundrum. Do I lie so he doesn’t feel bad and continue to let him believe that I get off by being licked in the same manner that he would attack a popsicle if he was stranded in the desert? Or do I crush his hopeful spirit by telling the truth and offering instruction on how to put the cream on the cupcake? Decisions, decisions.

“What Do You Think About These Shoes?”

I can spot a pair of fake red-soles on a girl from thirty yards away. But dude shoes? Who cares? As long as they fall into one of the acceptable guy shoe categories – boat shoes, flip flips, dress shoes, loafers, athletic sneakers or casual sneakers – and aren’t some weird color or bedazzled or something, I really have no thoughts about his footwear. That holey tank from his sophomore year spring break he insists on wearing around the apartment? That’s another story.

“Have You Gained Weight?”

“Do you have a death wish, asshole? Wait, why are you asking? DO I LOOK FAT?”

“What About A Threesome?”

I’m inherently insecure. So much so that I’m going to spend the majority of any relationship that I’m in wondering if I’m good enough – pretty enough, smart enough, sexy enough. The second a dude asks me if we can bring my hot friend Jacki into the bedroom with us, I’m immediately going to defcon 5 of relationship (and self) doubt. Even though it’s more likely that he just wants to reenact something he saw during a spank sesh. Wait, he watches porn when I’m not around?!?!!?

“Did You Ever Hook Up With (Insert Name Of Your Hot Guy Friend That You Totally Banged Here)?”

“No.” Always no.

“Will You Still Love Me If I Lose My Six Pack?”

“Yes.” Always yes.

“That Time of The Month?”

“No, I couldn’t possibly be in a bad mood because of work or family or any variety of other reasons! Of course, there’s no way my crappy attitude could be because you actually did something wrong! IT MUST BE BIOLOGICAL!”

“Am I The Biggest Guy You’ve Ever Been With?”

Do I tell him that he is and let him think that stubby pencil is actually a mighty sword, or do I tell him no and deal with his self-doubt? We ladies have struggled with this question since the dawn of time, and I am no closer to a resolution than anyone else.

“Have You Seen The Remote?”

All I wanted to do tonight was sit on the couch and watch five episodes of Real Housewives of Orange County. Being a semi-rational human being, I have to admit that it’s cruel and usual punishment to subject a guy to hours of watching rich white women drink wine and bitch at each other. But the other, slightly insane part of me decides I don’t need to tell him that the remote is under my sweatpant-clad ass cheek. He can get up and change the channel if he doesn’t want to watch Bravo, assuming he can even figure out how to change the channel on that space-like contraption that is the cable box. Meanwhile, I’m watching Vicki and Tamra talk shit about Heather.

“Do You Think I’m Losing My Hair?”

You know how girls are insecure about the size of their ass? Or how flat their stomach is? Or really any part of their body? Second to their disco stick, I find that most men are oddly insecure about their hair follicles. Like somehow the number hairs on their head is directly related to the number of little swimmers in their spunk. So even if I do see a slight receding hairline, or the tiniest appearance of a bald spot, the answer to this question is and always will be a resounding, “No!”

“Want To Order Pizza Tonight?”

My diet says no, but my heart says yes. Why must he always ask me these impossibly difficult questions?

If you liked this, check out “Questions You Never Want Your Girlfriend To Ask You”

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Jenna Crowley

Jenna used to be known as 2NOTBrokeGirls, but then one of the girls actually went broke, so she's struck out on her own. Jenna spends her free time saving the world, one sorority girl at a time (usually while wearing yoga pants), questioning why she decided to get a doctorate, documenting her love of all things cheese related, and hosting the new PGP podcast Don't Take It From Us. You can ask her anything you want about football, using your boobs to get what you want, and pizza at @JennaLCrowley on Twitter or via email at

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