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


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.

Then again, I’m the guy who wrote “Why You’re Still Single: Things Your Friends Would Tell You If You Promised Not to Get Mad”, so take whatever I say with a grain of salt, would ya?

Let us know how it goes.

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  1. 41
    Cute Redhead

    Meant to say “connect the dots.” And ignore the typo in the penultimate paragraph of my previous post. Guess I’m not in that 0.1%. Thank god I have other charms. 🙂

  2. 42
    Cathouse Teri

    I’m with Karl R on the whole “suitability” issue. There is nothing wrong without asking a dating expert a dating question regarding a friend. Neither is there anything wrong with looking for the variety of views that can be drawn from said expert’s readers. Since Jeff is a man of God, so to speak, he may simply be following biblical instruction. “Without counsel, purposes are disappointed: but in the multitude of counselors they are established.” And yes, this venue certainly provides plenty of anonymity. I have no idea why this must even be addressed, because I thought it was a given. Maybe vino is a plant, set up to stir up strife that doesn’t exist.

    So, back on topic I go. (Before vino brings out the Comment Police Badge and slaps on the cuffs for a-wandering!)

    Dan’s issue is not his weight. There are plenty of overweight men who are attractive and have no trouble finding women. Dan’s issue is that he doesn’t want to do the personal work that is required to accomplish living his own life the way he wants to.

    Jeff can’t help him with this. There is a tendency for a pastor to feel this is his job. To help people improve their quality of life. And to feel you have failed when you can’t. Then there is the seeking of counsel. And then, at some point, you have to just sit down with your own heart and your own head and realize that you probably knew the answer all along. Admit that it’s not your problem and this “little one” must make his own way. And work out his own salvation.

  3. 43
    Michael Ejercito

    I am effortlessly thin, as are a lot of people that I know.

    I guess it is the exercise.

  4. 44
    Karl R


    In a real life situation, determining that a person’s intelligence is in the top 0.1% is generally an educated guess based on the evidence.

    In this case, I learned that the lady in question had started college 2 or 3 years before the norm. Starting college 2 or 3 years early is pretty uncommon. I don’t have any stats, but I’d say it’s a safe guess that fewer than 1 in 1,000 people accomplishes this.

    A previous girlfriend of mine had started college at the age of 14.

    If you know someone’s IQ (I don’t even know my own), then the top 10% will start around a 125 IQ, the top 1% will start around a 140 IQ, and the top 0.1% is going to start around a 150 IQ … but this will vary with the standard deviation of the test.

  5. 45


    “what people were saying”? Jeez! What concern of theirs is her weight?? One can’t help but wonder sometimes the magnitude of character deficiency we are surrounded by.

    You bring up a great point, though (I sorta didn’t mention it myself earlier because I thought it was a given): the LW should -not- take it upon himself to “enlighten” his friend on his chances (and, really, at 35 the friend should be able to draw his own conclusions), only retire himself from the matchmaking.

    Michael Ejercito,

    “thin” isn’t exactly a good look for a man. (Something to deflate your arrogance a bit, hopefully.)

  6. 46

    @Michael Ejercito

    After checking out your myspace I can see that you’re only 30, and you’re Asian. Frankly, I’m not surprised that it’s easy for you to be effortlessly thin. You have a genetic advantage, consider yourself lucky. There are people in this world who don’t have that same advantage. Don’t put them down because of that. They are not overweight because they are lazy or gluttons, their bodies are just different than yours. I have to exercise every day of the week to keep my body at a healthy weight. So does my sister. We have overweight parents. If I relax even a little bit, I start to gain. I’m not obese, but I very well could be if I decided that I just wanted to relax and enjoy my life for a year without daily trips to the gym. My sister has decided to become a personal trainer and kill two birds with one stone.

  7. 47

    A very disheartening thing I’ve learned from this blog as well as internet dating is that we only want people to think of themselves the way we think of them. And when people have a higher opinion of themselves than we think they should, we are only too eager to put them in their place — you think you’re a size 0, well you’re really a size 6; you think you’re an 8 out of 10, well you’re really just a 5; you think you are curvy, well you are really just fat and you should say so. In effect, we have decided that our opinion of people is always true and accurate, but theirs is not. The question I would ask is that if we can’t accurately assess ourselves, why should we believe that we can “accurately” assess others? But even if we could assess others accurately, the really, really difficult question is when and why should we believe and value someone else’s opinion over our own?

  8. 48


    I don’t remember if it was on this site or some other discussion board that I saw the words “criticism is really just our own insecurities redistributed.” Priceless comment, priceless.

    But you reminded me of this one guy’s internet profile in which he said that he would no longer agree to meet women who don’t send him their pictures (this was some years ago when perhaps digital cameras weren’t as common), and that the self-description “trust me, you won’t be disappointed” would no longer be accepted. I remember I was just floored that someone had the self-esteem to describe themselves that way (I would think a guy would be completely justified in expecting a Linda Evangelista after a proclamation like that), and that he actually was disappointed. =)

    Karl R,

    neither formal education nor IQ scores are reliable measures of anything (and I am saying this as a person with a supposedly “genius” IQ). A lot of people are just narrowly gifted. I have encountered non-intellectual Ph.D.’s.

  9. 49
    Evan Marc Katz

    Eda brings up a really great point, although I’m not sure it’s disheartening. It all depends on whether you think ignorance is bliss.

    Is it better to be like Dan, who is obese and socially awkward, but sad because he can’t find a model to date him?

    Or would Dan be better off if he had a more realistic assessment of himself and had the ability to court a similar partner?

    Thus it’s not really about whether you’re a “5” or an “8” but whether your self-appraisal is analagous to others’ opinions.

    Self-esteem is useful to help us weather dark times and rejection.

    But when self-esteem is the SOURCE of rejection – when our egos dictate that we can’t find a partner because we overestimate themselves – well, I think it might be healthier to see ourselves as others’ see us.

  10. 50

    Where do I write with a technical suggestion?

    Anyway, please create a blog archive with article titles (as links) only. As it is, it takes too much navigation to find anything.


  11. 51


    Perhaps YOU should read the post again. It made mention of the fact that shallow Hal would text him 4 times a week. That pretty strongly implies that shallow Hal here is putting the burden on his friend to find him a woman. It became his friend’s business when he made his dating/love life his friend’s business, and thus the friend has every right to ask for advice… Also, you are assuming that this guy used his friend’s real name, which may/may not be the case. Either way, there are plenty of Dans in the world…

  12. 52
    Karl R

    Eda (#47),

    I’d like to add to something that Evan said (#49)

    Years ago I discovered that one person’s 2 is another person’s 9. That realization helped me transition from being a teenager with a low self-esteem to being an adult with a very healthy self-esteem. There will always be women who find me attractive … and some of those women will be attractive to me. Unless I’m interested in a woman, I generally don’t care whether she thinks I’m a 1 or a 10. If I am interested in a woman, her opinion becomes highly relevant.

    This morning I was flirting with the woman next to me in my yoga class. At that moment, her assessment of me was “accurate”, and nobody else’s (including my own) was relevant. Tomorrow I’ll be going on a first date with another woman. At that time, her assessment of me will be “accurate”, and nobody else’s will matter.

    This is a good reason to avoid dating women who are easily swayed by other people’s opinions.

    JuJu (#48),

    Your statement about intelligence is correct … up to a point.

    Obviously, you’re trading completeness and accuracy for the sake of brevity … as was I. If this were a forum instead of a blog, I’d love to continue this tangent through private messages. (I’m sure it would be fascinating.) Under the circumstances, I don’t want to stray further off the general topic.

  13. 53

    Based on what I read in Jeff’s letter, I don’t know if Dan has an unrealistic assessment of himself. Jeff doesn’t say that Dan thinks he is hot stuff with a killer personality. What I thought Jeff said was Dan thinks he can win a woman he finds attractive by dressing well, having a nice car and giving her gifts. Based on what a lot of the guys on this website believe, Dan isn’t too far from the mark. Perhaps he doesn’t need to lose weight, he just needs to make more money…a lot more money. Also, Jeff said that Dan is comfortable around people except the women he finds really attractive. Does that really make Dan some socially backward freak? If so, I guess I am a socially awkward freak too because when I’m around a really attractive guy, I get tongue-tied too. Fortunately or unfortunately, I don’t often have the opportunity to date men that I find really attractive. I only get to date men that are presentable….that’s my new term for nicely groomed, neatly dressed, normal looking guys for whom I have not one iota of physical attraction.

    I also question the notion that going after people who you don’t find attractive but who are closer to your own attractiveness level will make you more successful. In my experience, that tactic doesn’t really guarantee success either. I remember doing an experiment that crushed my ego. Since I was having very little luck with getting the attention of guys I found attractive, I decided to contact guys that I didn’t find attractive and guess what? I didn’t get their attention either. So, if I’m going to be ignored, I might as well be ignored by an attractive man instead of an unattractive one!

    Juju, I just recently had an experience where I agreed to meet a guy who didn’t have a photo who told me he was very good looking and had been highly sought after because of his appearance. So, I was really excited to meet him. When we met, I was so disappointed because he was not attractive to me at all. While I was polite and respectful on the date, I was so angry and I kept thinking on what universe would this man be described as very good looking. I kept wishing that he just told me the “truth” about his appearance. But that’s also when I began to wonder what right do I have to get angry with him for believing that he is attractive? What right do I have to feel that because I think he is unattractive he should think he is too? Maybe other women do in fact think he is very good looking. Are they right and I’m wrong? Are they wrong and I’m right? I think the answer is we are all right.

    In my mind, self esteem is the sentiment that you like yourself and who you are…warts and all. So, I believe that self esteem is not only useful to weather dark times, it is essential if you want to live a vibrant, happy life on your own terms.

  14. 54
    Evan Marc Katz


    The articles archive is called SiteMap. Check out the link at the bottom.

    Go crazy.


  15. 55
    Cute Redhead

    Well, one good thing to come out of this particular thread — at last we are discussing men’s physical attractiveness as an issue in dating, perhaps debunking the myth the “men are visual” (which implies that women are not). I notice that people are suggesting that this guy lose weight or “settle.” Much the same advice a woman in his situation would receive. No one is suggesting that the solution to his problem is to go out and make more money. I take this as a postive.

  16. 56

    In a way you are right. Looking above our means does have the potential to be harmful and create a lopsided as you would say “matchmakers dilemma.” But if someone wants something bad enough, who are we to tell them they cannot achieve it. Now, more than likely, if Dan isn’t willing to change his behavior and the way he thinks, he will continue to have the same lack of success he has always had. But if he decides to look inwards and tackle those inner issues that may be causing social awkwardness, introversion and low self esteem-he may be able to change his mind and his body in so much he becomes attractive to those 10’s that he so desperately covets. However, I have a feeling that his desire for ‘superficial’ beauty is a fantasy that would die once it became a reality. It’s often very hard for a person like this to relate to a so called ’10’ because they very rarely share the same experiences in life. It’s not just the physical discrepancy that makes for unhealthy, lopsided and generally short lived relationships. It’s also lifestyle and commonality. When these don’t coincide, rarely does it work out!

  17. 57

    Cute Redhead Jun 29th 2008 at 07:46 am 55
    Well, one good thing to come out of this particular thread at last we are discussing men’s physical attractiveness as an issue in dating, perhaps debunking the myth the men are visual (which implies that women are not). I notice that people are suggesting that this guy lose weight or settle.

    I was one of those people. I do think men are primarily visual and women are primarily attracted by who the man is. However, I think both sexes are motivated by both of these forces. The difference, IMHO is the degree and which force moves which sex more…..and….first.

    Yes, women do notice and appreciate good looking men.

  18. 58


    Post #18. Thanks a TON for the stats. I’m actually quite pumped up about making it a goal to beat those stats. I’m that convinced I have found the right system for maintenance. FWIW, I’ve had a “slow metabolism” all of my life. Actually, I like to think of it as a “fuel efficient” metabolism :). Women who I tower over, even non-athletic women, eat more than I do. I don’t have the “man card” in regards to weight control.

  19. 59

    @Selena, post #15. I just got back from my first trip to NYC as an adult this weekend. I can’t imagine living in NYC as being a hindrance to getting unsingle. I saw more beautiful there this weekend just getting around then I have in the last 3 months.

    @cute redhead, post #19.
    I’m not a Ken Doll or a 10, but I think I have the same issues you do although to a lesser degree. If it wasn’t for gay men and a few good close, married female friends who could be honest with me I could have gone through my life believing that my appearance didn’t inspire anyone. I agree with you about how much a change of clothing, hairstyles, and make up can do. I’m still amazed by that. FWIW, once I get past the initial attraction thing I find the company of “tom boys” very enjoyable. With regular women and “girly girls” part of me feels like I have to be an entertainment committee and a Ken Doll.

  20. 60

    @John, post #37
    Your experience reflects why I believe everyone should fight their emotional reflexes and make people giving them constructive criticism feel welcome. Sometimes people need to be told, but it is thankless job most people will avoid. When someone takes the risk of experiencing what you did, they should be thanked.

    @Karl, post #31
    My quote was out of context. I don’t believe that Jeff shouldn’t help Dan, but that he should help Dan by making sure that a reality check sinks in.

    @xpuff, #20
    Thanks for the stats! I think I will make my 1 year and 5 year goals. My system has already prevented me from backsliding several times and it has done so painlessly.

    Jeff didn’t write that he thought Dan was shallow, only that he was shallow in regards to how he approached dating women. Obviously he sees Dan’s other, good, qualities or he wouldn’t be friends with him. I think Jeff is one hell of a friend. Very few people would do as much for a friend as Jeff is. This is a dating advice site, so I think Jeff is on topic. He is seeking dating advice for his friend.

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