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

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.

Join our conversation (88 Comments).
Click Here To Leave Your Comment Below.


  1. 61


    I hope you do! What is your system, by the way? I’m always looking for ways to help make healthier eating a long-term habit and would like to check it out.

  2. 62

    @xpuff, post #61

    There is an ongoing study called “The National Weight Control Registry”. The participants are volunteers who have lost a significant amount of weight and who have kept it off for at least year.

    The people who run the study have found that the volunteers who maintain their weight loss do several things in common. They all frequently monitor their weight, they monitor their food intake, and they exercise regularly.

    I personally weigh myself every morning. I then enter my weight into a web site that computes a 5 day weighted average of my scale weight and computes a trend line on a graph that “data smoothes out” fluctuations due to water weight shifts. This gives me a steady weight reading. The trend line gives me an early warning I can use to fix problems while they are small. Which I have done several times……ahem! I’m 5 months into maintenance and this system has kept me from backsliding at least 4 times. It doesn’t sound like an appetizing way to live, but I swear it is [b]painless[/b] and even satisfying.

  3. 63


    Cool, I’ve heard of that. I keep trying to follow the things recommended by the registry, the weighing myself daily, writing down what I eat, I just can’t keep it up…I’m working on it though. Exercise is the easy part for me, that’s no problem. If only all it took to be thin was exercise, hah!

  4. 64
    Cute Redhead

    With all due respect, Steve — I am a woman. I talk to all of my woman friends about their dating/romantic lives. Men’s looks matter to us! The way a guy dresses and moves and talks and how he takes care of himself are what attracts us gals initially — same as with you guys. Maybe in the old days, before women could support themselves for various societal reasons that we don’t need to get into (again), a woman might opt for a provider over a looker. Nowadays we of the dating/mating generation want someone who’s gonna do it for us. And I don’t mean paying the bills and taking out the trash. Though a well-rounded…skill set is also appreciated. 🙂

  5. 65

    @Cute Redhead, post #64. I believe I posted a message earlier basically saying the same thing you did,

  6. 66

    @xpuff, post #64

    I had resistance when I started doing those things. I never figured out why. The logging was painless and took less than 10 min a day. Could imagine how rich you could become marketing a book that promised people they could lose weight by doing nothing other than taking notes for 6 min a day?

  7. 67

    Dan might have a little success learning pickup without re-wiring his head or slimming down, but ultimately he won’t come anywhere close to his potential (or come close to getting 9s and 10s). A lot of the PU guys call this having a “thin veneer of game” painted over an otherwise lousy personality and physical presentation.

    My first piece of advice is that he get his ass to the gym, ASAP, and lose the weight. I recommend fitness for everyone, not just guys that are 75 lbs over. Being fit and living healthy lifestyle gives you a better quality of life and a longer one at that. Dan’s first concern should be whether he’s going to have a heart attack before 40, not if he can score with hot chicks. Oh yeah, if you work out regular you look better too, don’t want to forget that part.

    @Mike: Want to agree with your comment in #28, a kick in the ass is the best way to go!

    @Seduction: great point in #58. Even if he could attract a 10, he’d never keep her! Her value would plummet just walking down the street with guy.

  8. 68

    I lost 80 lbs and I have kept if off for two years. And I think another very important way to maintain a healthy, active lifestyle is to hang around with people who maintain a healthy and active lifestyle. When your friends exercise and watch what they eat, your social activities are less likely to be centered around food and eating.

    The other thing I find helpful is to not limit being active to the gym. Choose the active route every chance you get…walk to work, take the stairs, etc. All these things add up and really make a difference.

    Steve, do you really feel that in today’s society, an overweight woman needs to be told that she would be more successful with men if she lost weight? You think that one more disapproving voice added to the voice of the magazines, the voice of tv, and the loudest, most disapproving voice of all — her own voice — is really helpful? When I was overweight, there was not one day that went by in which I didn’t loathe myself and my body…not one day went by in which I didn’t think all would be right if I could just lose weight. I would not have welcomed a friend adding to my misery by telling me I would be so much more valuable in this world if I were smaller. I would not have wanted one more person to telI me that I just wasn’t good enough. So, I don’t think telling a friend you’re fat and you need to lose weight is tough love or a necessary, life saving intervention. I think it’s just plain mean.

  9. 69

    post # 64

    Of course mens looks matter to women. Women talk about their relationships (they tell everyone) like men share stories about the latest automobile/hot rod/motorcycle they bought.

  10. 70


    Um, last time I checked, “Dan” asked “Jeff” to find him a chick. He did not, however, ask “Jeff” to publish “Jeff’s” opinion he’s fat and unreasonable to the entire internet. They are 2 separate issues, not related at all. It is “Jeff’s” fault he lacks the stones to tell “Dan” to shut up & find his own chick. But nooooo, he couldn’t do that. He has to tell the whole internet he thinks “Dan” is fat, balding and unreasonable. If I had great friends like “Jeff” I’d get my fanny into therapy pronto, right after decking “Jeff.”

    BTW, I thought preachers were supposed to keep confidences, akin to a doctor, or attorney. Some preacher “Jeff” is. Glad I haven’t told him my sins… The lack of discretion is shocking.

    Notice “Dan” didn’t invite the internet into his life, but “Jeff” did. Additionally, “Jeff” provided sufficient detail about their church group, demographics, etc, that If I were in the community (and I hope this letter wasn’t posted elsewhere, like yahoo, etc), it wouldn’t too difficult to deduce the subject of the letter.

    “It became his friends business when he made his dating/love life his friends business, and thus the friend has every right to ask for advice”
    — I disagree. It didn’t become the internet’s business. It’s between the 2. Nothing more. If “Jeff” has so little discretion, he should be roundly shunned.

    “His senior pastor has had counseling sessions with him to no avail.” – “Jeff”
    – How discrete. Love to confess my trouble there.

    I’m seeking dating advice for my friend Danielle. we take part in many church activities where I am the preacher and organizer. She does lots of activities with my wife and I. She’s at least 75 pounds overweight, has a moustahce, has the personality of a potted fern, and has horrible body odor. How do I make her see she probably won’t get the athletic, successful, good-looking investment banker?

    If you’re Danielle, I’m sure you’d love that manner of ‘helping.’

    “Nowadays we of the dating/mating generation want someone who’s gonna do it for us. And I don’t mean paying the bills and taking out the trash.”
    – Ya, that’s why women NEVER care about how much $ a guy makes….*gag*

    The ‘we’ referenced is the huge minority.

    See other threads for basis of sarcasm.

  11. 71
    Hot Alpha Female

    I think when it comes to dating and finding a partner that you really need to find someone who is more or less your equal in many respects.

    I don’t mean to say that they are exactly the same person as you. But in terms of values, beliefs and life ambitions. Therefore i see your point when you talk about the level of attractiveness.

    Because here is the thing. If you are some FAT SLOB who can’t be bothered to get off their butt to work out and dont really respect your body. Then how in the world do you expect to attract some gorgeous babe, who does respect her body, loves going to the gym and staying active.

    I would say that if you want to attract those kind of people, then you have to do your best to be a PERSON that they would date.

    Now i will say, that just because someone isn’t that attracttive .. say a man .. does not mean that he can’t get a hot sexy ass girlfriend. This is also very possible too. But there is a little work involved too

    Hot Alpha Female

  12. 72

    @Eda, post #68;

    First congratulations on your 80lb weight loss. I lost 48lbs over the course of last year and I know that it is not an easy thing to do.

    Second, I don’t understand your comment as “Dan” the overweight friend is not a woman.

    Third, you are mistaken if you think, even on an unconscious level, that you or women in general own the psychological pain of being overweight in today’s society.

    Let me tell you, you don’t.

    As I wrote earlier, I have always had a “fuel efficient” metabolism. To stay slim I have had to eat less than many (small) women I know. I have been heavy several times, including during my formative years. I have received the mean comments. I have been ignored. I have had people I’ve been romantically interested in fall for who I am, but not sign up for anything more than friends because of my appearance.

    Yes, heavy people know they are heavy. As a formerly heavy person I know that people can know they have a problem, find it too painful to face, and push the awareness out of their minds on a daily basis. The problem is those days add up and all of us only have so many days in our lives.

    Jeff’s friend Dan knows he is heavy and he probably knows he has other problems as well. If he is like most other human beings he is distracting himself from his awareness of it as an issue. I’m not advocating that Jeff insult Dan, but that he makes sure that Dan hears …..once….. that he has a limited amount of time to enjoy life…..and that if he doesn’t want to miss out he has to start doing things about his problems, including his weight……now.

  13. 73

    @Lance, post #67 reminds of the adage that the best way to begin attracting someone good into your life is to get your own life in order, for yourself, first. That and the other adage, that people tend to attract what they are. People with stuff happening in their lives tend to find/attract people with stuff happening in their lives.

  14. 74

    Jeff, if you are still reading the comments, I think Selena’s post #15 has the second best advice given so far. Once Dan is convinced he has to move under his own power having him read this blog and other related dating books/materials will give him the reality checks that he needs.

  15. 75

    Congrats on your weight loss too, Steve.

    In my post I was actually referring to your response to John, the man who told his overweight female friend that she needed to lose weight. That’s why I said who needs to tell an overweight woman that she should lose weight. You responded by indicating that people should invite more constructive feedback from others.

    I agree that women don’t own the pain of being overweight, but I think the penalties for women for being overweight are greater than they are for men.

  16. 76

    I was told, that a woman loses her figure, intentionally, simply because, she gets tired of dealing with all the different personalities she attracts.

  17. 77

    I think the real issue is that Dan is afraid of being in a relationship so he places roadblocks. He’s done it for so long that he’s settled into his comfort zone. It’s not a matter of facing up to being a “3” or anything…it’s having unrealistic expectations of what a relationship truly is. As a result he’ll never be happy because he’s not giving himself a chance.

    I’ve seen overweight people be in happy relationships with skinny folks of either gender…this shouldn’t be a discussionn of 3’s trying to date 8+’s, it should be one about Dan getting his act together.

  18. 78
    elaine benes

    @ evan –

    maybe the dingo ate your baby. 😉

  19. 79

    It sounds like Dan suffers from self-esteem issues. My 2nd cousin always dated (and twice married) women who treated him very badly. He also struggled with his weight since childhood. Then, a couple of years ago, he had gastric bypass surgery. His marriage ended, but he got full custody of his kids and has since started seeing a woman who treats him very well. He also gets lots of positive feedback and attention from the ladies where he works, and I’m sure this has done wonders for his self-confidence. My cousin was always the nicest guy in the world, with maybe a little too much faith in the goodness of others. He was down on himself b/c of his weight so he attracted the kinds of women that deep down he felt he deserved (i.e. women who treated him badly, abandoned him, were abusive to his kids, etc). Losing the weight resolved a lot of his self-esteem issues, and I think that would really work for Dan as well. Dan is clearly going after women he already knows deep down will reject him. Why? Because deep down he feels he deserves to be rejected!!! Get Dan to deal with his obesity, and work on himself a bit. This would be so much better than just railing at him to pick uglier women. Sorry to be blunt, but I think this isn’t about Dan’s market value in the dating world, it’s about his psychological issues. And as Karl pointed out: it depends which market he’s in. There isn’t just one monolithic dating market (unless you mean the online market). There are many “niche” markets in the “real world” (i.e. offline) where Dan could realistically be more competitive. Encourage him to take a yoga class, and/or join a gym that is coed but has a higher ratio of female members to male.

  20. 80

    vlh I totally agree. But I don’t think the issue is weight in of itself; in your cousin’s case, losing weight helped him realize he person inside aned boosted his self-esteem, which is great.

    If Dan loses weight it may not have the same result, but I agree that by working on himself in a way that would boost his esteem levels (new sport, hobby, training for a running event for charity, or whatever) would be a big plus.

    I knew this guy once who always complained the women he kept meeting were mean and bitchy, and he was such a great guy w a heart of gold. Truth be told, he always went after the mean girls, then broke up w them after 6 months, but whenever he met someone who was a better match for him, he’d end up sabotaging the relationship and getting dumped.

  21. 81

    Just reading old posts here…

    Karl R, if you’ve never had your IQ tested, how can you know you are in the top 1% in intelligence? Are you using some other kind of measure, or are you from Lake Wobegon?

  22. 82
    Karl R

    Joe asked: (#81)
    “Karl R, if you’ve never had your IQ tested, how can you know you are in the top 1% in intelligence?”

    It’s where I routinely tested on other standardized tests.

  23. 83

    Joe 81 – sometimes, people have their IQ’s tested prior to employment opportunities.

  24. 84

    There is nothing — NOTHING — more attractive than someone who is joyful and interested in other people and things. Dan (and the people who are so interested in manipulating his life for him) need to get over this “find a gorgeous mate” nonsense. Let Dan join a non-church (new people!) organization that does active things that he enjoys, ideally in big groups. What is his passion? There is a club or class going on somewhere near him that is made up of there people who enjoy that, too. 

    Dan may be depressed. He might need more exercise and sunshine to help with that. And you know, Dan may be setting the bar so high for female companionship as a way to avoid women; he might be gay — or he could just be one of those people who isn’t all that interested in joking up with anyone. He seems pretty locked into a scene that isn’t serving him well. A change is in order.

Leave a Reply

Your email address will not be published. Required fields are marked *