I’m not sure why this particular question (or any variation on the theme) seems to absolutely baffle most men…but it does, so I really appreciate receiving this topic from a man!
My typical question has always been, “Honey…do I look fat in this outfit?” And I swear nothing has consistently sent my man into a complete panic quicker than those eight little words.
And I’ve really never understood why.
For years when I was married, I would ask the question and Brian (my ex) would visibly cringe and then daggers would seemingly fly from his eyeballs and he would mumble some kind of incomprehensible huff and walk away as if he considered the matter closed. And I was left wondering if that meant I did or did not look fat in the outfit? (Note: Never a good start to an evening out.)
These days, Matthew (my boyfriend) says that I’m simply not allowed to ask those types of questions. He considers them to be:
“Loaded questions with absolutely no possible right answer in sight”, or
“Land mines waiting to blow up in his face”, or
“Evil, hateful attempts to send men into the fiery depths of hell.”
I think most men feel the same way.
But I disagree.
And so I’m grateful for the opportunity to give men the secret to providing the right answer…
WE DON’T REALLY WANT THE TRUTH.

We want reassurance. We want to know that we look beautiful to you. That no matter what we put on our bodies…you LOVE OUR ASSES in it!
The truth is that by the time I come to my man with any of these questions…I’ve pretty much made up my mind about what I’m going to wear and I’m just looking for a compliment when one isn’t forthcoming.
There. I said it. I’m fishing for compliments.
So for me, the correct answer to the question “Does my ass look fat in these jeans” is quite simply… ”HELL NO honey! Your ass is what makes those jeans look great!”
Oh and guys…none of that mumbling the words without looking at me bullshit. I want you to turn around, look at me in those jeans, and say those words with absolute conviction.
Do it and I’ll be one happy puppy.
Now…there are times when I really do want my man’s opinion on an outfit. Not a shallow compliment (see? I’m admitting that I know that’s what I’m fishing for above), but his actual opinion on what looks good and what does not. Take last week for example. I tried on a dress I was going to wear for a family Bar Mitzvah in Miami over the weekend, and I really couldn’t make up my mind on the shoe/necklace/earring combination. So I called Matthew upstairs and asked his opinion.
Wisely…he asked “Are you really asking my opinion or do you just want me to tell you how good you look?” (Obviously the man is starting to know me).
“No honey, I’m giving you choices and I REALLY WANT YOUR OPINION. I have this sexy black dress with a hot pink liner that peaks out as I walk or spin…so I want the whole look to be perfect!”
Cautiously he agreed to help.
So we started with the shoes…of which I was wearing two different styles on each foot. I did the classic lift one shoe up at a time to showcase two very different black evening shoes and without hesitation he picked the one on the left (a lovely black satin shoe with crystal ankle straps). Thank you very much Matthew. That was perfect!
Then we moved onto the jewelry. First, I tried on a large pink crystal necklace & a pair of delicate diamond-like earrings and he hesitated and asked if there were any other options. He said it seemed unbalanced. OK…we instantly stepped onto shaky ground as this was my first choice, but I was willing to work with him to get it “balanced.” So I tried on option #2, a delicate diamond-like ball on a simple white gold-like chain with delicate (i.e. small) diamond-like earrings. This time he thought it wasn’t enough. In fact, he thought the delicate combination was a bit “too old” looking (quickly adding that I didn’t look old…but the jewelry made me look older – SMART man).
Clearly that wasn’t going to work, so we kept at it. HE then suggested putting the large pink crystal necklace back on, but with a pair of larger dangling diamond-like earrings and WHALA! It was perfect.
And I knew it was perfect because he stepped back and a huge smile came across his face and he said those magic words…”Babe, you look beautiful.” And I knew he meant it.
But if I had pulled the whole thing off on my own, and uttered the question “Honey, does this dress make me look fat?” I hope that he would turn and look at me, and without hesitation say “Babe, you look beautiful.”
And I think now he always will.
I think I’m pretty logical when it comes to this question. I‘ve been known to ask it, or a variation of it, from time to time a lot.
The truth is that if I’m asking the question in the first place, I already know my ass looks too big or my dress is too tight or I’m wearing something that just doesn’t look good.
I’m actually OK with Mike telling me the truth. Really, I am.
(Notice that I say “Mike”. The situation that I’m referring to is when your loved one or someone you’re close to asks this question, not someone you don’t have a good or close relationship with. If someone asks and they’re not a loved one who you have a good relationship with? Lie. It’s not worth the hurt/drama/crap. And let’s face it: odds are that they’re fishing for a compliment anyway. And if you’re the asshole who asks these questions of your friends/acquaintances/strangers (you know who you are), cut it out. Please, stop making others feel uncomfortable with your “do I look fat?” or “how old do you think I am?” questions.)
(Ahem…)
I’d rather Mike tell me before I walk out of the house looking less than awesome. If I ask it, I’m already thinking I should change, and his answer will usually just sway me one way or the other.
(Or his answer is irrelevant and I’ll do what I want anyway.)
Granted, if Mike ever looked at me and made a gagging sound or some horrid comment, I’d probably punch him in the throat.
Hell, even if he said a simple “yes” in response to the above question, I’d probably kick him in the knees…or at least cry a bit.
Thankfully for both of us, he’s very polite and tactful (and I’m not really that physically violent).
I say that the key here is to stay polite. Go ahead and tell them the truth… nicely.
I’m a big fan of “that’s not the most flattering thing you could wear”.
Or “it looks nice, but not great”.
Honestly, I appreciate that…
If I ask for his opinion.
Let me say that again, this time in all caps: IF I ASK FOR HIS OPINION.
If Mike just looked at me and said something negative about my outfit without my asking for his input… I’d probably cry.
This especially goes for people other than Mike. If a girlfriend were to walk up to me and tell me my ass looked too big, without my asking her opinion, I’d have a problem with that.
If someone walked up to me on the street and said I didn’t look good – even if they said it politely and then gave me a few bucks and also handed me a brand new puppy – throat punching would be imminent.
So, only say something if you were asked your opinion. Otherwise, keep quiet.
NOTE: be careful about the context. If you’re loved one asks this question in reference to something that he or she has no choice but to wear (for example a bridesmaid dress or a work uniform), say they look awesome. Say they look amazing. Say they took your breath away. There’s nothing they can do about the situation, so don’t do anything to make it worse.
It’s also important to say that I never ask this question unless I truly want the answer.
(No, really.)
If I ask it, I accept the response. And I’m very clear about my intentions when I ask.
Before we left for Miami last week, I tried on the dress I was planning to wear and asked Mike for his honest opinion. Mike looked at me, smiled, and said I looked great, BUT the dress didn’t look perfect. He said that the fabric fell wrong in one place, but other than that I looked good. I was already a little iffy about my dress, and let’s face, “good” wasn’t gonna cut it, so I changed into a different dress. This time, he said I looked amazing. He told me I looked fabulous. He said he wouldn’t change a thing.
Without his honesty, I would have never tried on another dress, or felt nearly as confident.
I don’t ask these questions because I’m fishing for compliments, or looking for an ego boost. When I was discussing this question with another woman (not my mother), she said she didn’t believe me. She said that all women ask men these questions as a test or as a reason to hear how amazing they look.
But I honestly don’t. Why? Because the odds of that little test backfiring and resulting in a huge, horrible, messy argument just isn’t worth it to me. In the beginning of our relationship I probably did play that game, but now? I’ve learned my lesson.
If I want a compliment, I ask Mike how I look. It’s simple, it’s to the point, and he always tells me I’m beautiful.
And a lot of times? I don’t have to ask.
(I feel the need to point out that you have to figure out what your significant other is really saying when he or she asks these questions. In discussing this topic with many women over the past week, it seems that my thoughts aren’t shared by many other ladies. Maybe take another woman’s (<——-) advice? At least to start with? Because I’m not going to be responsible if you go tell your girlfriend/wife/friend-with-benefits that her ass totally looks huge and then scream “BUT ALLY THINKS I SHOULD BE HONEST!!!” while she’s beating you with her hair dryer.)