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New Rule: If I Think Her Friend Is Cuter, I Can’t Date Her

December 29th, 2010 Leave a comment Go to comments

Back in November, I asked my readers what was the best way to approach a girl whose friend I already tried to date unsuccessfully. While some commented encouraging words and noteworthy ways to solve this predicament, the vast majority of them emphatically told me don’t even think about it.

After much consideration of their words against me trying to date the friend of a girl I already failed to date, I have to say I agree. But admittedly, my reasons aren’t as noble as subscribing to some made up girl code most women want to try and administer upon me. The reason why I will no longer try to date the friend of a girl I already tried to date is because I have decided I will no longer date a girl with cuter friends in the first place.

See, it actually pisses me off whenever it happens, and I know plenty of other men will agree.

We meet a girl we find plenty attractive, and step to her accordingly. Third or fourth date, things are going well, and she gets this bright idea to have us meet one of her “besties” for brunch or drinks or something of that ilk. We oblige, get to our destination, notice some fine girl already there, sitting at the bar. And automatically, we’re hoping, and praying that is not the friend of the girl we’re already dating. Then, the girl we’re dating walks in a beeline straight towards this fine (very fine) girl and squealing “HEEEEEYYYY GIRL!”. Now the two of them are hugging, and we’re wishing we were in between the both of them like some sort of human sandwhich. Then introductions are made, and we’re hoping this fine girl doesn’t want a hug, but as it turns out, she goes in for a hug. Now we have a slight bulge in our pants from the embrace, which then goes from slight to full as soon as we sit down and this fine girl takes off her jacket to reveal some serious sweater cleavage. And because of the way we’re sitting, we have to face the sweater cleavage for the entire meal.

Now do we see how this gets frustrating?

Had we known the friend looked the way she does, and had we met the girl we’re dating alongside her friend, the truth is, we probably would have tried to approach her friend. This is nothing against the girl we’re currently dating, she’s plenty cute too, but she obviously isn’t the gold medal in her group of friends.

If any of this sounds way harsh, let me just say this is a reality men might have to face too. I know for a fact some women out there go through the exact same thing I just explained above, only in reverse. They start dating a guy who is moderately attractive only to meet his friends who are way more attractive.

I think both genders can agree how disheartening this discovery can be. All of us want to date the best looking one out of the bunch. Just like no one calls “back window” before they call “shotgun” when they get in a car, no one calls the second cutest looking person in the group before they call for the cutest one.

But as I have learned, sometimes, we can’t always get the cutest one in the group. Sometimes they don’t want us, or they aren’t available, or they just weren’t around before we started dating the less cute one. Sometimes the circumstances are accepted, until we realize the cuter friend is also the type of friend who is always, always around. Now we have a situation in which we’re constantly reminded that a few weeks ago or a few months ago, we jumped the gun. We cashed in a little too soon and as long as we’re dating the one who we cashed in on, while they continue to hang out with the girl we should’ve held our cards for, we’re going to be reminded of this fact.

I definitely expect people to disagree with a lot of what I wrote here, if not on the basis of points, principle. And trust me, I get it. I would hate for a girl to stop dating me all because she gets  flustered whenever I bring one of my friends around. But if I got upset, it would only be because of how brutally honest she was about her feelings, which is something I can respect. Besides, I’d do the same thing if I met her much cuter best friend.


The Process: Due to a storm in Northern California, my flight was canceled. I now will be leaving on Thursday to head back, but not to NYC, to Boston, where I will take a train to NYC. Drama.

The Poppin’ Questions Podcast is going up tonight. Link soon. 

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  • ashley

    i understand the idea but don’t completely agree. the friend may be cuter but she also may be crazy or have psychotic tendancies, if that’s the case you’re better off staying with the one you have! no need to cut off the lady you have because she’s “80 %” and her friend is “95 %”. the grass isn’t always greener…

  • adrina hinton

    So if you are 3-5 dates in with girl X and then find out girl Y is cuter, how do you plan on dropping girl X? Do you think you are ready to be THAT honest with people in 2011? No judgment on this post, I think being honest is being great. This reasoning sounds great in theory, but if you’re going to carry it out you’re probably going to need some sort of plan. Either you plan on early group dates, or you have a great way to execute this “termination process” after you have met THE friend that you speak of in your post. Ive met THE friend though, and been mad as hell too! Can’t lie: I tried talking to both before. Didnt work out in my favor though! lol

  • Dancinggreenapple

    My bf is over a decade older than me (in years, not youth ;). Most of his friends his age are already married with wives who have post-baby weight, no longer care about being sexy, etc. When we do group dates, I admit that I don’t dress as sexy as I would if it were just he and I. Not because I think his friends want me, but just out of respect for them and their relationship. I say all this to say: If the cuter friend knows she is usually seen as more attractive (and 99% of the time she does know), she should also try to be a little less appealing when meeting her friend’s bf. Cleavage falling out and giving hugs that force a woody is a bit much.

    Sooo, while the post made me cringe a bit, I do understand where you’re coming from…BUT the matter is just as much an issue of the boyfriend needing to stay focused as it is the cuter friend being a bit more considerate of the obvious.

  • Jeff Toliver

    But have you ever been in a situation where you are dating a chic…but then you might meet her friend who looks just as good or better and your chemistry with her friend is 10 times And you wish you had have met her first? Sometimes she doesnt even look better than the one you are dating but yall just click from the beginning..smh Its hard out here

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  • Kae-Toya


  • Sharelle Ivy Manansala

    I get it… This post to me seems more so “for your entertainment” though. I was in this boat once upon a time where my boyfriend’s homies were 10s but damn, I loved my man.

    But being serious: I TOTALLY get it if you are a casual dater and NOT looking for anything serious that you wouldn’t “want to date” someone JUST because their friends are cuter. Also kind of a bit shallow, no?

    However, if a person is the type to date in hopes of finding their happy ending, this is just ridiculous. It’s about appreciating what you’ve got already. I mean… especially if you’re taking that person out on a third or fourth date I’m guessing one has to be feelin’ that person to invest so much time. If you’re always constantly looking for the next best thing, and following all these damn rules and percentiles and blah blah blah…. you’re gonna end up alone.

  • Aisha

    Hmm, i get where you’re going with this and i am so close to agreeing except, aren’t you eliminating a lot of beautiful women just cause there is another beauty in her close circle? I don’t know, sounds like a male ego thing which I don’t think I will ever fully understand. Perhaps a better title would be “I will no longer date girls if I wanna sleep with their friend”…I mean that is essentially what you are saying, right? 🙂 That makes more sense…I get that.

  • Daree

    Does this rule go for even casual dates? So what is the solution? Do you now scope out a love interest’s friends before committing to her? I agree with the last 2 posters as well.

  • Rachel

    I already knew you were a bit shallow, but seriously? ‘Cuter’ can’t be the determining factor in deciding whether to continue dating someone you may have gotten to know past just the outward appearance. What if the less cute friend laughs more, is kinder has more integrity etc?

    If physical beauty means so much to you, good luck with staying faithful in your next relationship.

  • Alexia

    A lot of pretty girls go around in packs these days- adds to their appeal on a night out. So you might have to ask her on the first date whether she is honestly the best looking girl in her group!

  • Mandi

    What if the cute friend can’t cook/is self absorbed/lacks depth/intelligence/is promiscuous/is controlling/has annoying habits?

    Cuteness should not be the only measure you use to determine if a prospect’s friend is better suited to yourself than prospect herself. I believe your criteria extends beyond that.

  • Amanda

    If you have taken the time to go out with a woman four or five times, that means that you must like her. When is it enough for you? There is always going to be someone out there better looking if you are looking. Just appreciate the good thing that you have and appreciate the beauty in others without trying to hook up with them. Geez man, you are gonna have a hell of a time finding a wife if what you have is never good enough for you and it always seems to be about looks for you. You have too many damn rules. Just go with the flow and focus on the one in front of you.

    P.S. I like your blog.

  • Mr. Write Now

    any women who’s mad at this post, is the less cuter friend.

  • Rogue Thought

    I have a few questions of my own…
    Why should a woman make herself “less attractive” to make someone else feel better? Wouldn’t she be making herself feel bad in the process? In addition to that someone else is determining what is attractive. A woman with makeup may be attractive but as many men have stated in many places at many times sometimes a women looks better with no makeup. So it is possible to become more attractive in the attempt to become less attractive.
    And women are always told if you’ve got it flaunt it…unless it ends up tempting someone else. Well if that’s the case you need to get new friends and/or let your man know that you don’t like the way his friends are looking at you (or be a man and tell your girl.) Not that they aren’t going to notice. The friends should know what they are like and capable of doing.
    My last question (…I think) is what makes a date? Is it a date everytime you see each other? Are you expecting a commitment after date two? And what are you doing on these dates? Would I want a man to drop me because he saw one of my “cuter” friends? Nope not in the least but I also know if he was/is more compatible with me or her. (…and if he left me for her he would soon see that…and I’d smh and then laugh.) He was not my boyfriend, we never did anything, and it’s his loss.
    …ok I think I’m done. Thank you.

  • wahoo4uva

    I don’t disagree with anything in the post because nothing said was incorrect; however, I do find it as limiting as it is harsh. It’s also reflective of how shallow we’ve become. I wonder how many more relationships would endure if we evaluated the whole of what our options have to offer us BEFORE deciding which person we want to date. I think this would allows us to get to know who the whole person really is rather than creating in our minds who we want them to be or assuming who they are and deciding he/she is more/less desirable to date based on physical appearance. Yes, we do this. Without even knowing it. The more attractive someone is, the more positive assumptions we make about him/her. Then when the person doesn’t live up to those assumptions and expectations, leading to conflict in the relationship, often followed by a breakup, we wonder what happened. Why didn’t we see it coming? I thought he/she was this/that, but is entirely different. I was way off with that one. Come to think of it, so-and-so (less cuter option) was probably better for me. Well, yeah! DUH! Your selection process wasn’t holistic to begin with, so of course you’re just now coming to this realization that your other option was likely better in the bigger picture. I recommend reeling in the physical attraction (a natural response, but it can be overwhelming if he/she looks that good to us), then spending quality time getting to know someone on a platonic level before deciding we wanna date them. It may help save us from being disillusioned and disappointed later on. It’s a theory.

  • maria

    ” I know for a fact some women out there go through the exact same thing I just explained above, only in reverse.”

    I just imagined a cute guy saying “HEEEEY BOY!” haha.

  • maxfab

    And this is why I don’t have any friends who are cuter than I.
    Just kidding!
    Well, not really.

  • Aqsoul

    Maybe you should try getting his name correct before trying to hate

  • Kae-Toya

    Men like to think they can always punch above their weight. There is nothing wrong with wanting better, but this post makes Jozen come off flighty/ditzy as hell. Men don’t like women they like the idea of having a woman, for whatever the reason they desire the woman.

  • Kae-Toya

    Men always want to hold out for the 20% and woman need to realise and understand this concept. Guys ———–> How are you supposed to find time to get to know someone when the person you are interested in, is looking for the next best thing?

    Jozen make up your mind are you shallow and conceited or not?———> you’re confusing me.

  • SimplyBeautiful

    ‘spending quality time getting to know someone on a platonic level before deciding we wanna date them. It may help save us from being disillusioned and disappointed later on. It’s a theory. ‘

    It’s a fact :-). I recently decided to switch gears with my thinking when it comes to men. As much as I want to be in a relationship, I don’t want to waste my time on someone and he’s not feeling me. We’re on the same page, yet reading two different books.

    So all I have to offer is the cultivation of a friendship. I need to learn you the whole person to make sure not only you are who you say you are, but you are emotionally where you say you are as well.

  • Kae-Toya

    Tayrin dear his name is Jozen.

    Aqsoul………it is called having an opinion.

  • Aqsoul

    Hmmmm. Is that what Tayrin was expressing? An Opinion?

  • Kae-Toya


  • Nynos81

    This was a very good comment. Thanks

  • coco

    Hmmpf! The eyes are forever seeing and wanting. Shallow, immature. Grow up.

  • taut_7

    i don’t think i’ve dealt with a woman who wasn’t the best looking woman in the group of friends. i have dealt with a couple of women felt like ALL their friends were good looking but i knew that was a lie.