My Unattractive Best Friend Is Completely Shallow! How Do I Help Him?

A fat man exercising at the park

I have around 25 people that I speak/preach  to on Sunday mornings and I stay in contact with through church services or email. Truly, I can foresee that someday any or all of my single students (ranging in age from 22-55) could find the right person, with one exception. Dan is a very overweight (at least 75 pounds), 35 year old male who is quite interested in sports and is somewhat involved in church activities.

What I felt where at least 2 wonderful potential female matches have come along for him to pursue; however, his response is always the same: “I am not attracted to them”, because these females have similar physical characteristics that he has.

Dan is truly one of my best friends and often does activities with my wife and I and our 3 children. His taste in women is so superficial that if an attractive female were to show any interest in him (despite any other similar characteristics) he would leap head over heels for her, and I am afraid would be in deeper trouble.

He sadly does not have the personality it would take to win the type of girl he is dreaming of.   He feels very comfortable around men and ladies that are older and younger. However any girl anywhere near his age or that is the least bit attractive, he cannot even bring himself to speak to her for a lack of confidence. I have advised him that he must compensate for his lack of physical attractiveness with personality, yet he feels that having a nice car or dressing sharply or buying a girl flowers or candy should be all that is required to win the heart of a prospect.   He regularly (4 times per week) will text me to ask if I have found him a woman. I have known  Dan for 20 years and truly don’t know how to help him. His senior pastor has had counseling sessions with him to no avail. Any suggestions?



I know this guy in Los Angeles who is successful in the entertainment business. He doesn’t have the issues that your friend Dan has — no social awkwardness, no obesity – but he is short, heavy and balding. Anyway, a couple of years ago, we were hanging out with friends on a hot July day, and we were watching women go by. I pointed out an attractive brunette passing by on a bicycle.

Just because you’re attracted to a George Clooney or a Angelina Jolie doesn’t mean you have the ability to date them.

“Nah,” he said. “She’s not my type.” I was shocked. I wasn’t aware he was in the position to be so choosy. Oh, but he was. In fact, this man made it very clear that it’s the hardest part of finding a girlfriend was that nobody’s attractive enough for him. He’ll only date women that are “8’s” on a scale of 1-10.

Later that night, we were at a bar. I was chatting up a beautiful woman in her mid 20’s and we spotted my guy friend across the room. “On a scale of 1-10, where would you rank that guy?” I asked her. Without hesitation, she answered:

“He’s a 3.”

If that’s not dating in a nutshell, I don’t know what is.

Despite our iffy self-esteem, we tend to overrate ourselves in terms of what we “deserve” to date. Just because you’re attracted to a George Clooney or a Angelina Jolie doesn’t mean you have the ability to date them….

After years of witnessing this phenomenon, I actually gave it a name: “The Matchmakers Dilemma”.

Simply put: Most people are 5’s, but they want to date 8’s.

This is why it’s so hard for a Matchmaker to set anyone up.

Because most people don’t think they’re 5’s. Or 3’s. In other words, most people are delusional.

(Sorry to be so crude as to rank people with numbers, but it’s shorthand to describe someone’s physicality and most people can grasp the concept, so…)

In the big bell curve of life, for every 10, there’s a 1; for every 9, there’s a 2; and so on. Most of us are going to fall somewhere in the middle of the bell curve — 4, 5, 6. Most of us are average.

Then why can’t we come to terms with it? Not everyone is of equal attractiveness. Not everyone makes the same living. Not everyone has the same sense of humor. Not everyone is equally personable or kind. Yet we certainly wouldn’t admit that we were below average on any of these things. We’re all Mother Teresa, we all look great for our age, we all love to laugh. Just go on a dating site. You’ll see.

My fiancé quotes an old Friends episode where Joey says that people are allowed to date within 2 slots of themselves. Thus, if you’re a 7, you can date a 6 or an 8. Any more than that, somebody’s slumming.

When I work with clients online, pretty much all of them put the most attractive people on their favorites list. It’s hard to blame them. Why write to “the 4” when you can write to “the 9”? Yet even dozens of rejections later, many still refuse to grasp the fact that they’re overreaching. They feel they deserve a 9.

“I can’t help what I’m attracted to,” they say.

“I can get people like this in real life,” they say.

“I’m not dating anyone short/old//heavy,” they say.

Doesn’t matter if they’re short, old, or heavy. They want what they want.

Dan needs to come to terms with the idea that beautiful women have the option of going out with men who are younger, cuter, thinner, taller, funnier, and more confident than he is. And while it’s no crime to be attracted to a Maxim model, it’s not a very realistic goal for him — or for the majority of American men.

My fiancé quotes an old Friends episode where Joey says that people are allowed to date within 2 slots of themselves. Thus, if you’re a 7, you can date a 6 or an 8. Any more than that, somebody’s slumming.

Any hot woman who dated Dan would be slumming. Which is why he needs to get in touch with what he can command on the open market. It really hurts to say this, but apart from a handful of wealthy men who can attract a hot golddigger, there are few folks who can overcome obesity, lack of personality, and social cluelessness.

If you’re a true friend, Jeff, you should tell Dan the truth. That to get a hot woman, he’s got to slim down. That he should hire a dating coach or study some pick-up artists. That setting him up with your church’s finest would be a disaster for all parties involved.

Let us know how it goes.

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  1. 1
    Cathouse Teri

    I think Dan needs to do a lot more than slim down. He needs to quit being a putz. It’s like trying to help someone who is in an abusive relationship. Only in Dan’s case, he’s abusing himself… with his own delusions. And has gotten quite used to it. Why bring a partner into his abusive world? Do the world a favor and tell Dan you can’t help him. He’s on his own, regarding women. If he hasn’t learned anything from by now, he ain’t gonna.

  2. 2


    If you want to help Dan you are going to have to risk offending him. You are going to have to burn 3 messages into his brain:

    1. People who will settle for nothing other than perfection get just that – NOTHING.
    Nobody is perfect to be around, not even 10s. He has to learn to accept others for his own happiness. The best way for him to do that is to start accepting himself. That will help his other issues too. I recommend “Overcoming The Rating Game” by Dr. Paul Hauck. After that, research Dr. Albert Ellis’ concept of “Universal Self Acceptance”.

    2. He is 35. He doesn’t have all the time in the world left.

    Time and opportunities pass fast at his age. He needs to get moving right now if he doesn’t want to lose out for good.

    3. Nobody can help him.

    It is possible for him to lose weight, improve his confidence, improve his social skills, and improve his personality. All of those changes are only possible if a person has strong internal motivation.

    Nobody can push him into these changes. Not even you.
    Give it a good try for your own peace of mind and accept whatever comes.

  3. 3
    Karl R

    Jeff sounds like he’s part of Dan’s problem.

    Dan texts Jeff “4 times per week” to see if Jeff has found him a woman. Jeff has only found Dan 2 potential matches, both of which were unsuitable for Dan. But by perpetuating this charade, Jeff is allowing Dan to pretend (perhaps even to himself) that he’s doing plently to find a woman. Jeff is supposed to somehow magically find a beautiful princess that will happily fall in love with and kiss the frog.

    It’s time for Jeff to tell Dan that he’s stopped looking. Put the burden of the search back onto Dan. Then he’ll at least need to start talking to the women … as well as taking all the other necessary steps.

    In addition, Jeff is worried that an attractive woman might show a little interest in Dan and he’d fall head over heels for someone who was otherwise completely unsuitable for him. SO WHAT !! Dan is 35 years old. He’s allowed to make some bad personal decisions. If the decisions have unhappy consequences, then he might learn something from the experience.

    Overall, I agree with Evan’s assessment of people wanting a mate who is an 8, 9 or 10. But I’ve figured out a couple ways around that particular hurdle.

    Years ago, my first serious relationship was with a lady who was distinctly better looking than I was. At the time, I was probably a 5….
    But I was this lady’s type. On her scale (lanky), I was probably a 9.

    I can also make use of this the other way around. If most men consider a woman to be a 4, but I see her as a 7 or 8, that works in my favor. And the guys who are “chubby chasers” have it made. Their 9s and 10s are most guys’ 1s and 2s.

    And to follow up on Evan’s observation, that people will say, “I can get people like this in real life.” I’ve certainly found that to be true in my life. I tend to meet women at church, at the yoga studio, or at the dance studio. All three locations lack single men around my age. And if you broaden the range to single men of any age, I’m one of the youngest and best looking in all three locations. Relative to the competition, I am a 9.

    Of course, I’ll also highly recommend getting in shape and building self-confidence for Dan or anyone else. If you improve yourself from a 5 to a 7, your odds of dating an 8 increase dramatically.

  4. 4

    I noticed that you quoted your fiance in this story. Congratulations on your engagement! I hope that you both live a very long and happy life together!

    Take care,


  5. 5

    I was totally with your advice until I got to the part where “Dan needs to slim down.” I like most of your advice but maybe you need to revisit the statistics on weight loss–that even if Dan was one of the lucky few who lost weight there is a 99% chance of him regaining it back within five years. So if he managed to slim down and attract a hottie, in five years if she is as shallow as he is, she’ll be unhappy in the relationship.

    To find lasting love he should look for someone who’ll love him for what he looks like normally and come to the terms that she’s probably not likely to be a model.

  6. 6

    ha, ha 🙂 I also noticed the fiance! Congratulations to both of you!

  7. 7
    Dating Headshots

    “Because most people don’t think they’re 5’s. Or 3’s. In other words, most people are delusional.”

    LOL! You sure know how to tell it like it is.

    1. 7.1

      Billy Joel sang about the uptown girl…I think he had talent, but I think Christy was out of his league and they didn’t last.   The couples that last somehow look like each other after years of being together, ha.

  8. 8


    Do you actually have those statistics? I ask because I lost 48 lbs last year with a system that I am convinced provides an answer for maintenance. I started looking for stats so I could make 1 year and 5 years goals. I couldn’t find anything as gloomy as you allude to, at least not on the web. If you have recent, gloomy stats, I would appreciate having them.

  9. 9

    Yah, congrats on the soon to be ex-single dating exert thing.

  10. 10

    Jeff, Evan;

    You both describe men would not be attractive on that 1- 10 scale and you both describe pointing attractive women that they would have a chance with. How can these women be attractive if they are at the same level of attractiveness as your unattractive male friends?

  11. 11


    that’s because most people’s approach to weight loss focuses on the external, whereas the only approach that would work permanently is cultivating self-love and self-respect. It’s not the weight that’s the problem. I mean, it certainly can be, just like many symptoms of various diseases can be enormous problems in and of themselves, but the weight is exactly that – a SYMPTOM of a problem.

    Anyhow, this particular guy does not sound like he has much to offer regardless. The four messages a week demonstrate a clear lack of social graces, and the lack of discernment – issues with self-worth.

    And I am sorry, but the letter is so poorly written that I had trouble understanding it. I, too, do not think it shouldn’t become his friend’s problem, and especially in a case that appears like the blind leading the blind.

  12. 12

    I agree with others here that giving him back the reins is the best way to go. If you feel that your friendship can stand it, give him a brutally honest assessment of where he’s going wrong. If not, then send him to online dating (Evan lists some Christian dating sites and there are also things like Equally Yoked, if sharing a religion is a requirement) and let him find out on his own.

    To be honest, your portrayal of him makes him sound like he has Asperger syndrome, in which case behavioral therapy may be more helpful than a friend’s advice, however well-meaning. Ultimately, as long as you make it clear that you are not actively seeking for him (though you’d of course pass along anyone’s info that you happened upon) because HE should be the one actively seeking, then you’ve done what you can do.

  13. 13

    As Evan said, we all overestimate our own attractiveness. If you don’t want to be the blunt killer of whatever self-esteem your friend has you may want to send him to where he can submit his photo and people will rate it based on attractiveness (and other qualities). That might help reduce the swelling around his head, and perhaps make him more realistic about his options.

  14. 14

    Now that Evan is engaged, that just means he has another ex-girlfriend 🙂

  15. 15

    A less blunt way would be to refer him to this blog and have him read past entries. Then he will see that just about EVERYONE has some of the same issues when it comes to meeting the perfect partner. Too short, fat, ethnic, too attractive, curvy, old, virgin, experienced, shy, live in NY, live in a small town, live in a rural area, make under x$ a year, worried about golddiggers, ambitious, not ambitious, religious preference, divorced, never married, want kids, don’t want kids–on and on.

    The diverse opinions on this site can be good for a reality check sometimes. Or at least to let you know…You’re not alone out there even though you’re single.

  16. 16

    Why on earth is this even a topic?

    What flipping business is it of Jeff’s (OP) that HIS perspective is his friend is shallow? Why do so may people who are married/involved actively campaign to play matchmaker? To compound matters, he tells the world (internet) he thinks his friend is shallow.

    Some friend. Glad I don’t know him.

    Stay out of it. It’s NONE of Jeff’s concern, or ours. Period.

  17. 17

    Whoa there, vino.

    You seem to be a little emotional on the topic. Overreacting a bit there? Can’t imagine why.

    *laughs gently into sleeve*

    It *is* (the newly affianced!!) Evan’s job to give advice.

    I do find it interesting is that peoples’ “numbers” don’t seem to be reflective of their personalities in this discussion. It’s all looks! looks! looks!

    By my calculations, even if Dan went to Zegna for a complete makeover and the gym for the rest of his life, he’d still be a “3” ’cause his personality’s just that odious. (And I’d bet a decent percentage of those hot size 00 blonde “9”s y’all are chasing would agree.)

    But I’m a girl. We think about these things. I guess it really *is* only looks that matter to the guys here.

    BTW, Steve, you didn’t ask me specifically for them, but here are your gloomy stats. There are about 53 links there for your perusal:

    A small consolation – it’s easier for men to keep off than women, though, because your bodies aren’t programmed to store fat for kids like ours are. (Not that you all generally give us a break on that scale, or offer to watch the kids for the hour and a half it takes to work out and get in and out of the gym, or anything.)

  18. 18

    It’s peculiar, I personally never rate the men I date with numbers. I just think in terms of who is attractive to -me-.

    Isn’t assigning a number – a way of gauging how others will react to your choice?

    Nor would I describe myself as any particular number, especially since I’d rate my face and body differently.

    A-L, I looked at a few faces on that site and I think this format and the opportunity to anonymously blurt out whatever comes to mind brought out the worst in me (and apparently in others too, from some adjectives I saw). Not sure I’d advise anyone to “establish their value” this way.

  19. 19


    Someone already beat me to it, but check out this link too:

    A great book on the subject is “Rethinking Thin” by Gina Kolata. The actual science of losing weight is contrary to all conventional wisdom on the subject.

    Congrats for losing 48 pounds, that’s a great achievement and hopefully you’ll be one of the ones that beats the statistics.

  20. 20
    Cute Redhead

    I kinda have the opposite problem — maybe. You can tell me. I’ve never had trouble finding some to date but felt insecure about my hotness — you know, there is always someone thinner and sexier, etc. I will grant that I am cute. 🙂

    I haven’t done the internet dating thing too much, but decided to give it a go through one of those compatability sites. Holy smokes–now I see what I have been missing. I have been dating so many guys, and so many want second, third, who knows how many dates — it’s a bit overwhelming! Am I cuter than I thought? I have to say that this time with the dating I am paying a lot of attention to the way I dress (I’m kind of a tomboy, so that was never my thing). Who knew that a dress and a pair of heels and some eye makeup could take me so far.

    Also, I have to add that I really like each and every one of these guys. And here I thought I was a man-hater. A tomboyish man-hater. Turns out I make a little concession to girliness and end up with a whole slew of nice guys who have a lot going for them and would be good boyfriends or husbands. Who knew?

    Now the problem is — how do I choose? What a problem, eh?

    Thanks for reading!

    1. 20.1

      I love Cute Redhead’s post.   It’s off topic insofar as most of the discussion has been about how to interpret Dan’s overly critical standards, but like Cute Redhead, I was caught short by the claim that most people shoot too high because they think too highly of themselves.   Is that true?   I’m gonna play the numbers game just for the sake of argument:   I am a 5.   Maybe a 6.   I won’t even contemplate that I could be in the bottom half of the scale, even though I understand that half the world must be.   But I routinely date out of my league.   Ticking through the committed relationships I’ve had in my life, those guys were definitely a 10, an 8, a 3, a 5 with a particularly sexy baritone, a 10 whom I married, and another 4 who recently dumped me (as sweetly as you can dump a person).   I WAS slumming when I was with the 3, but for reasons that had NOTHING to do with his looks.   And I’d have been SO lucky to keep the 4.   I dunno, we give a lot of ink to the idea that people, and men in particular, are super shallow about looks, but in my experience there are an awful lot of people out there are who are open-minded and genuine and willing to look at the whole person.

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