Jack

Most of the time, I’m a deep and thoughtful person who considers whatever you say very seriously.

But when you ask me, “Do I look fat in this?” My brain goes on auto-pilot. IT doesn’t matter what you look like squeezing into that size 0, I automatically say “No, babe you look great/fine/cute.”

I hate to be a liar (and nine times out of 10 in this case, I’m not lying), but I just don’t see the benefit of answering the question honestly. If I say you look fat, I may accidentally cause you to throw away your best and most expensive outfit.

Secondly, I know exactly what you really look like. Your most slimming black outfit won’t suddenly convince me that you look like Giselle Bundchen, and your blouse that’s white with horizontal stripes won’t fool me into thinking you’re the same size as Queen Latifah. What does it matter what you look like?

Most importantly, I’m nearly certain that I’m the only person you are going to ask this question. This means that if I answer it honestly and say that you do look fat, then I’m the person who’s insulted you the most that night, and thus the person that you will be the least happy with, at least subconsciously.

The real question is to you: Why are you putting me under this undue pressure? The person that you see in the mirror is pretty much what I see when I look at you.  You can see just as well as I can whether you look fat, and you’re undoubtedly your harshest critic. If you’re not sure whether you look fat, you almost certainly don’t. If you think you do, and are asking me for confirmation, that’s unnecessary, and borderline diabolical.

The point is this: there’s no right answer to this question. So why ask it? Why subject me to mental anguish, or worse, disengagement? Why not just let me admire you in silence?

I hate to ascribe ulterior motives to you, but when you ask the question, I feel like you’re testing me. And it’s a test that’s impossible to pass. Why else would you take the chance of asking me to either insult you or lie to you? There’s a reason why I don’t ask you if I look ridiculous when I’m in my extra-large St. John’s basketball jersey with skinny jeans.

I love you — I love how you look, no matter the outfit, and I want you to be happy. If you wear something that’s not so flattering, I’ll chalk it up to your generally excellent fashion radar being a little off. But I will never, ever  tell you that you look fat. Like, ever.

Jill

When I ask you “Do I look fat?”, I expect you to be honest, but not too honest.  I mean if I look like a cow, then yes, please tell me, but if you’re saying I look fat just because you don’t like my style, then keep it to yourself.

I spend too much time and money on my clothes. I buy all these fabulous dresses, skirts, shirts, jeans etc. because I love them. Trust me. I don’t waste my money on things that I don’t think would look good on me.

If I put something on and I don’t have to stare at myself for more than two minutes in the mirror, I like it. If you don’t like it, keep your opinion to yourself. All I’m asking for is for you to be honest when it comes to my weight.

Every girl whether she’s underweight, overweight or “normal” has insecurities. These insecurities can bring our self esteem down and even cause problems with our relationship.

Think about it, if you were uncomfortable in your skin, your insecurities could put a strain on our relationship. I ask you if I look nice because I care about us. I represent our relationship, and if I look bad, well then, our relationship looks bad too.

Sometimes I feel like I look good but it’s nice to have a second opinion. If my jeans don’t fit correctly, please tell me. The last thing I want is to look bad when we’re in front of people. If my stomach is popping out of my dress maybe it’s time to suck it up and buy an extra size larger.

When I say “be honest” I mean it, but don’t get carried away. The last thing I want to hear is that I look fat all the time. I want your honest opinion keep in mind, it still hurts to hear that answer. Yes, we can be confusing but if you really want to be with me, learning the secrets of how a woman thinks shouldn’t just be some annoying task.

I know you love me no matter what I look like, but it would kill me to be an embarrassment to you. When we go out with friends, I want to look good! Who wants their girlfriend to look unattractive when they’re with all their friends?

Yeah, yeah, beauty is found within, blah, blah, blah.  But I know that there are days where my shirt is a little too tight or my leopard print bra is showing through my white shirt and you’re thinking, “what’s up with this girl?”

I want to eliminate those thoughts all together and start having a more open relationship. Your honesty is the first step.

But only if I ask.