My title
Home > dating, Girls You Shouldn't Fall For, guys, s#x, women > Girls You Shouldn’t Fall For: The Confusingly Pretty Girl Edition

Girls You Shouldn’t Fall For: The Confusingly Pretty Girl Edition

I want to talk about a particular type of woman. She’s pretty, but not conventionally so, and though this woman doesn’t exist in my current dating life, she has popped up from time to time, not only in my life, but the life of all men.

If beauty is in the eye of the beholder, some of us be holding some confusingly pretty girls. That’s what I call them, confusingly pretty girls. These are the girls who we think is fine, but none of our friends, girl or guy, is co-signing. Maybe she’s aware of it, maybe she’s not, but every man knows the deal. They’re dating a girl only they think is fine, and all the while they’re wondering, “Damn, how did this happen?” Well, I’ll do my best to explain how it happens.

The prototype for the confusingly pretty girl? Oprah Winfrey. Beautiful to some, only looks good with makeup on to others, and to a chosen few, she’s so fine we watch her show naked. But overall, the woman has a lot of good stuff about her.

Contrary to popular belief, men aren’t entirely visual. Sure we’re suckers for the pretty face and the bodacious body, but attitude, charisma, and personality go a long way for us too. If the girl is quick with a funny comeback, knows how to party when it’s time to go out, and handles any attention she gets from the opposite sex with a certain amount of poise and charm, we’re getting sucked in. There may also be other things going for her, like she has a nice place or she has a powerful position, and we’re attracted to her stature.

And then we decide to start sleeping with the confusingly pretty girl, and as it turns out, she’s great in bed too. Now this really sucks because not only do we want to hang out with her more we also want to bang out with her more. We’re addicted to this girl who we know very few others find attractive, and we can talk all day about how no one should care what others think, but that’s how we end up getting the nickname Shallow Hal.

I’ve seen it happen before. No wait, let me go one step further. It’s happened to me before. I see a girl, lock eyes with her, she locks eyes with me, and I’m gone to go after her. Then we meet, she has all this personality and charm and I’m ecstatic to the point where my teeth are visible from across the room. Then I come back to my boys and they’re looking at me, say nothing, and then hand me a bar napkin. “What’s this for?” I ask. My boy says, “Your beer goggles. Wipe ’em off.”

How mean.

(It should be noted here, women have the Shallow Hal all the time. Even with me. I mean, yes, I know I’m a good looking guy, but I’ve dated a lot of women who thought I was only okay and were willing to give me a shot anyway. I’ve been that guy who hears, “Your girlfriend is so pretty” and never, “You two are a beautiful couple.” Oh well. Thanks to all you pretty ladies who took a chance on me. Now back to my rant…)

Now, we don’t care of course. Sure she’s confusingly pretty, but we’re not confused about what we are going to do. We’re going to go after this girl anyway, but in the back of our mind we know we shouldn’t. And why shouldn’t we? Because we know the minute a pretty girl ‚ the type of girl men and women find pretty — enters our peripherals, we might be off to get to know her better too. And that’s where things get messy.

Another messy thing we have to factor in is how a girl who is a 7, though possibly can move up to an 8, can also possibly move down to a 6 or even worse, a 5. This is something else I’ve experienced firsthand.

I met this girl who was confusingly pretty at a party my boy was throwing. I came from out of town, she was his neighbor. From the moment we were introduced I was into her and she was into me. We had the kind of chemistry that only comes along once a season. Now, through the lights of the place I could see this girl wasn’t crazy good looking. She was okay. Like I said, confusingly pretty. But to me, I wasn’t confused at all. I knew I wanted this girl and I knew I could have her. So I got her. And when I told my boy, he didn’t give me any props the next day. He just said, “Hey, we all have to get those out of our system.” I said, “What the hell is that supposed to mean?” He said, “You know exactly what it means.” I said, “Yeah, you’re right. I do.”

We hooked up and then went our separate ways, but managed to stay in touch. After all, like most confusingly pretty girls, she was awesome in bed, so I wanted to keep things in order until our paths crossed again. And they did. About six months later she was in my city for a convention and we made some plans to hook up. When I arrived at her hotel room, I was genuinely shocked. She went and did this thing with her hair that just didn’t fit her face. She cut it shorter.

Now I’m a sucker for short hair, but it’s only because I love pretty faces and short hair enhances them. But this girl, well, let’s just say she didn’t have the face for the short hair. Still, I couldn’t change my mind about what I came to do. As a matter of fact, I didn’t want to change my mind. That was the weird thing. Even though I saw this girl had downgraded, I still really wanted her. Like in the way I wanted supermodels.

After we were done, we laid in the bed catching our breath, and she says to me, “What do you think of my haircut? Be honest Jozen.”

Awkward silence. Then I said, “Oh I love short hair. That’s my thing.” One of those general answers a person can apply to themselves if they have enough sense.

“Really?” she said, sounding confused.”Be honest.”

“I am being honest!” I protested. “I really do love short hair!” Again, the general answer.

Then she says, “Well, I’ll be honest. I hate this haircut. I made a bad call. It looks awful and I can’t wait to grow it back.”

“Stop,” I said, though when I said stop, I didn’t mean stop being so hard on herself. I meant it more like, stop talking I’m trying to sleep.

“No,” she said. “I really don’t like it. As a matter of fact, I’m going to keep it real. I’m surprised you slept with me.”

Now I have a headache from the internal laughter I hear from all my boys.

She continued, “I thought to myself, ‘No way is Jozen going to sleep with me looking like this.'”

I wanted to beat myself up. Nothing confuses a man more than hearing a girl you just slept with admit she wouldn’t of slept with her if she was you. Confusingly pretty girls, man. Stay away from them.

For those who missed it, today is Until I Get Married’s one year anniversary. If you haven’t read it yet, click here.

  • IceQueen

    @**inquiring mind**
    I agree with you I never got it too, why men need to have their boys like or think a girl they are with is attractive either? They aren’t with her so what does it matter….I think that’s why the whole term “trophy wife/girlfriend” comes from. Lots of men just want an stunner on their arm but with not much else going for her just so they can show off to their boys and other men. Its quite pathetic!

    And yes you are right men really are mean!

  • brownivyx

    I think unless you’re in the 9-10 range, you’re going to fall into the CPG category…especially in a society in which the feminine ideal of attractiveness is so stringent. Also, one must take regional preferences into consideration. As a short, dark, Black woman with with short hair, there is a certain type of man who tends to skim right over me (which is fine cuz I’m not checkin’ for *that* dude either). However, every time I visit the Caribbean, or even certain parts of Europe, it’s a whole different game. Bottom line is, everyone is beautiful to someone…and out of that crop of folk, for a few the feeling will be mutual. Anything less is…well, passing time. Not that there’s anything wrong with that…

    Classic CPG: Cameron Diaz

    Classic CPB: Andre3K

  • Sunkissed404

    Cosign that…You nailed the CPG and CPB right on the head. lol

  • martine

    This was great. Lmao.

  • SB

    I just want to say that I love this part:

    “Now I’m a sucker for short hair, but it’s only because I love pretty faces and short hair enhances them.”

    I love a man that can appreciate me and my short hair! And at last check…I’m not confusingly pretty! LOL

  • Kimmy

    This was really funny and true. Great read!

  • leressa

    great post as always Jozen.

  • Ana

    This going to sound wierd but I think you still missed the point. I don’t think you get the point of the “confusingly pretty girls” or the “confusingly men” (in the womans case). Its a lesson there, and I think you missed it *shrug smh*
    But your thoughts were interesting

  • Idealistic1

    Wow!!! As disheartening as it is to say I’m willing to BET money that I’m confusingly pretty…because I’m quick to say that I think I’m a cute girl, but my personality puts me ahead of the pack. This was so eye opening (-:

  • Vonzell

    CPGs, CP people in general are interesting. I think it is that uniqueness that grabs you though – they’re all your’s in a way. To me it’s like popular novels. Everyone loves Harry Potter, so saying you like Harry Potter is nothing special. Everyone expected that. But that you like a warlock book personifying cats? Not many people like it. It’s cool to like something unique though. I hope that made sense.

    I think I’m average. I am a CPG. This doesn’t go to say that I have a low esteem – I don’t. I know what I’m good at, I know what I look good in, and I take care of myself. Some guys are attracted to me, some (most) aren’t. I used to really hate that about myself. I just came to terms with the fact this year. And now that I have accepted it, I wouldn’t have it any other way 🙂

  • dellbelle

    all i could do was cackle after reading this, b/c I can hear your “stop” in my head. like, no, really.. pls be quiet b/c you’re reinforcing my thought pattern. hahaha…

  • Pingback: Until I Get Married » What’s With The Face And Why Men Care About It()

  • Farida Mohamed

    hahaha too funny!

  • Stacy

    I may be biased because I’m not conventionally pretty. But I am good looking and have been told by many that I’m fine. That being said, this is the dumbest post I have read on this site and I hope that now four years later you no longer let dumb ass mofos who are clearly jealous dictate your happiness. I really hope you don’t care as much now that you are a few years older what people think about you or your girlfriend. Confusingly pretty? If you think she looks good that is all that matters.