Listen Live
Majic 102.3/92.7 Featured Video

How do you navigate the question “Does this look ____ ?” or “Does this make me look _____ ?”

As I mentioned in a previous diary, I’m no slouch. Some of my ex-girlfriends bring me to near tears when I see them years later looking like they just stepped off the Ms. Ivy League Black America stage. I mean, my good taste bites back at me when I see how gorgeous women only get better with time.

Luckily I date a young lady who’s an A-1 looker with smarts and sass to boot. Nothing about her makes me think ‘Ugh, I wish she didn’t wear that.’ Her clothes are in good taste, her makeup isn’t an excuse to take a face dive into a pile of powder and her shoes/feet have made male onlookers stand still in admiration. Alas, I appease my own vanity by being seen with one so fair.

But even the prettiest women will throw you a question about her looks every once in a while that makes you say ‘huh?’ No matter what anyone has told me about women needing honesty at any cost, it’s not accurate. Women do not (of course) want to be lied to about the important stuff (where you were last night, do you love me) but they absolutely encourage lying about things that will reassure them of how beautiful you think they are. Well…not lying, but embellishing to the degree that it will make her feel secure. And really, when you’re about to go for a night on the town and she’s spent the last 40 minutes debating which shoes go with what purse, you must take a stand. Whining about how long she’s taking will cause strife and the ‘yeahyeahyeahwhateverworks’ line shows your annoyance rather than your attention to her wears. Because, when it’s all said and done, you want her to look good when you go out — even if it means you’ll be watching her look even flyer after you broke up. (Sweet!)

Here are some stock tried and true exaggerations responses when she drops the “How does this look on me” bomb:

1. Does this make me look fat?

No, no and no. Nothing makes her look fat. Mind you, when she says “fat” her mind is channeling pre-gastric Star Jones fat. Some things may not complement her shape well. Some outfits fit snug in one place, but for you to say that it makes her look fat is errant. I’ve had the great fortune to date (and get dumped by) some slim, terrific women but, in the case that your lady is looking a little plump in her outfit, try:

The tight shirt or pants scenario level one yellow = tight but still well within her range of looking good:

  • “You know (So-and-So brand) ALWAYS runs small”
  • “I was thinking the opposite actually. Your curves are one of the things I like/love most about you.”
  • “Pssssssh, please! I know a thousand girls who would DIE to be able to fit into that”

Should You Date Your Ex?

And if you’ve passed your first test move to…

The tight pants level two orange = no skin is hanging out but there’s some crucial squeeze going on, she may even be walking funny:

  • “Turn around and walk in it for me, sweetie. I dunno, only because the club we’re going to, we’re gonna wanna dance a lot. We should swear stuff we can move around in.”
  • “First of all, those jeans/pants fit waaaaay better than when you bought them. You should probably wait for an even sexier occasion to wow ’em with that.”
  • “Damn…nothing like a good rear view of a woman so beautiful. If you go out and guys are looking at you in those, I might get jealous.” (Throw in a smirk here for good measure.)

The tight pants level three red = she should not be wearing these pants. They are from a long-gone era. They might pop a button if she turns/bend/steps too quickly just as a matter of physics.

  • “You are so classy girl. I wouldn’t want someone to think you’re into hoochie clothes. You stopped wearing those when you matured.”
  • “What if you have to pee?” (Appealing to her sense of logistics here will get points. You know the line for the ladies room anywhere will be foolishly long.)
  • “I think I see a tear in the crotch area…” (Even if you don’t, hint at the fact that she’s playing with loaded denim if she walks out in these.)

2. “How do you think I should fix my hair?” OR “Does my hair look all right or is it too crazy?”

Her hair is God’s gift to her and to you. It should represent who she is, team up with her eyes to be the first thing noticed when she walks in, and show her emphasis on both style and detail. Criticizing her hair is no small feat. You want to be honest about how her hair looks lest you risk endorsing Bird’s Nest chic. Still, there are ways to describe her hair as a strong attribute that you should think about.

Short Hair/Hair Pinned Back: “I like it when you wear it short. It accents your most delicate features like your cheekbones, neck and shoulders.” Add more compliments if she’s wearing her favorite v-neck sweater or a nice necklace. These accessories draw focus away from just hair and face. Notice how nice they look.

Long Frizzy Hair/Not-recently-coiffed Hair: “It says something about you that you can wear your hair out and still look ravishing. I can run my fingers through it. It’s like you’re taking a walk on the wild side with your confidence showing.”

Freshly Done Salon Hair: “Gorgeous. You have never looked so good. Is that a new style? Everything seems to work on you.” (Key point – make sure to have at least SOME familiarity with her last hairstyle. She spent hundreds of dollars on it and, despite what she says, wants everyone to comment.)

3. “If you saw me on the street in this, would you approach me?” Talk about a soft-pitch home run. I’m assuming if you chose her to be your long-term mate, you spoke to her without knowing her prior. This is your opportunity to reinforce how urgent you felt when you saw her. You don’t need to reminisce too much but letting her know what you liked then will translate into funtimepartycity for you now.

The Monologue: “Not only would I approach you in the street, I’d be somewhat intimidated by your grace and presence in my world. I remember how much my instinct told me to holler at you at first. I had all the motivation I could muster, and I was STILL nervous. You look more sophisticated now so I’m not sure if I’d be the one to talk to you on the street — maybe if a friend introduced us (?) Anyway, I’m not one to turn my back on destined acquaintances. I know if I didn’t come up to you then or now, someone else would. And there’s no chance he would appreciate you as much as I do. So to answer your question, yes, I’d talk to you a thousand more times because I know it’s not just your “look” that drew me in. Your walk has charm, sure. Your smile is bright of course. Your physique makes my senses awaken. But beyond all that, there’s something about you that could never be contained in an outfit. That’s what I’ll always find remarkable. Hopefully, you feel the same way.”

9 Stereotypes Of Black Men That Aren’t Always True