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    Kathy

    Can you do a pretend flirt and run your fingers through his hair, and then say in a golly gee tone of voice "Why, I LOVE your hair like THIS!" after you've tussled it? Or would he not respond well to a fake flirt? Or would he respond too well? Or perhaps you could say "I'm going to blah blah salon to update my hair (not that there's anything wrong with your hair, Dan), please come with me for moral support!" and then get him in a chair, too, and the stylist will have a go. Of course, you'll have to pre-arrange a take-down with the stylist.

    blackbird

    I'm getting that 'running your fingers through it' would be physically impossible - it's probably glued in place.

    I think you do do the bit above -
    but couldn't you also just level with him?
    Couldn't you just say something like:
    You are just the most attractive hunky guy and you need to UPDATE! The hair thing you have going makes you look OLDER!

    Give it a shot -

    I convinced my balding dentist (young and cute) to quit swirling his hair around...shave it right down to the wood? he asked, and I nodded. And then the following week I fell all over him and told him how cute he was.

    Karey

    I know it's easier said than done but perhaps you would be better off being honest with him?
    Just say something like "(Insert name here), I'm not being rude and I'm saying this in your best interest.. that combover really does nothing for you." then follow it up with a compliment like "I mean, you've got great eyes and I think you would look great if you just bit the bullet and maybe shaved your head?"
    Friends usually appreciate when another friend is being honest with them and surely having a combover would make him a LOT older looking than just shaving his head?!

    Dean

    This reminds me of the time I bought my mom a makeover for Christmas because I wanted her to pamper herself, and then she broke into tears and asked if I thought she was ugly and needed a makeover.

    In this case, I would talk about how hot I think bald guys are (which is true) and how I think that close buzzed look is really great... and then ask if he's ever considered it.

    But the truth is... if he thinks it looks good (maybe he does) he will probably be hurt if you go right in for the kill.

    Leo

    You could try some Phoebe to Rachel talk... when she finds out Rachel is being cheated on, she sits down and says "I make the most wonderful cookies ever". Rachel eats it and nods, so Phoebe goes "No you no I'm not a liar, right? He's cheating on you"

    Or, in a more serious tone, you could ask him to go to the hair dresser with you when you are going to get a haircut... and then you just say "Hey, why don't you try something different, just for a change? this guys has some great ideas and I trust him... maybe he can suggest some change for you"

    but yes, i would go with honesty anytime, just like karey said. Easier said then done, but... "donable". Trust me. This is from a guy who looked at one of his best friends and said "I'm sorry to be the one to tell you this, but no one else will... You're going beyond fat and it's getting hard to look at you".

    BTW, we are still friends. =)

    Chad A

    Shave his head in the middle of the night.

    Not subtle, but very effective

    The Aitch

    A friend of mine did that hair transplant thing (he went to Vancouver BC because it's like 20 grand cheaper to have it done there instead of the US) and within 6 months he had a full head of hair on his scalp and let me tell you this guy was Bizzald and did the combover. It looks awesome though. Not doll hairish or anything. Have him look into that. Otherwise, ignore it.

    Clem

    I don't think there is much you can do. When he is ready he will. You can always talk about getting older and what you loathe about it. Also, point out men who are attractive but have bad hair (esp. come-overs) and see how he responds. This may open the door to his own self-discovery that he has a come-over. Many victims of come-over are truly unawares for quite sometime.

    All else fails, make a pact to shave your head bald as a new year's resolution to begin again and ask him to join you. Only 8 weeks left.

    rio

    dont you think if hes taking the time to blow dry and comb over and spray he knows something bad is afoot, or ahead as it were. so if part of him knows hes doing something bad then he wont really be too hurt if your sublty hint to a hair cut.

    jim

    I'm guessing that your friends read your blog.

    So he's read this.

    I think you've already done all you can do.

    zjz

    Propecia really works! In like, 4 months. Even if yr shiny bald.

    Kamasutra Jones

    Don't know if you all remember Rudy Guiliani during those heady 9/11 days, but he had a combover then. Once out of office, and with his new wife, he got rid of it (without shaving his head) and looks great now. He doesn't look any older, but he certainly looks better. I agree with what your friends have said above. But, he'll only do it if he wants. Until then, you have to deal.

    David

    I don't know about a shaved head, but when I realized I was losing it up top, I asked the stylist what to do and he trimmed it very short. I still had hair all on my head, but since it was short, it minimized the areas that were sparse.

    dan

    re: Propecia--he's been taking it. Not working. No dice.

    ariane

    Now, I love my boyfriend. A lot. But...After our first date I came home and said to my roommates, "We've got to fix his hair."

    I've managed to do it, honestly. He has lots of curly hair but no idea what to do with it. I basically waited until one day when it looked good - it was messed up rather then him attempting to comb it into place - and I complimented it. Not so much as to reveal my agenda, but enough to make him feel good about himself. And every time his hair ever looked remotely like that again, I repeated the process. Eventually, it worked and his feelings were never hurt.

    Hope it helps.

    desertwind

    All the men in my family started balding early. Even the brother-in-laws! Only my husband has avoided the curse, though the distinguished grey started pretty early (tangent here -- his older brother uses Grecian Formula. Bah!)

    My dad did the combover (and a wretched mustache plus a super fab red Corvair convertible in his early 40s.). He kept up this charade and we never said anything to him about it. (well, we made a few loving jokes behind his back -- particularly as my brothers began losing their hair and organically learned to keep their hair short to avoid the dreaded Bozo-effect).

    Rambling here -- but, I don't think there's anything you can do for your friend. He knows.

    Scott

    I recently started losing my hair and it was I was traumatized. For years I had an enviable head of long thick jet black hair. When it stared coming out I felt like I was losing my best feature. I tried all the creams, potions and pills trying to to no avail. Finally, my best friend sat me down and with hand on hip said "Look, you're hot, you're not defined by your hair, it's going away but you're not. Clip it short and then go botox the hell out of your face if you still feel old." I did both and he was right! I can't blink but I look much better.

    eek

    Combover is no time for subtlety. This is a personal grooming emergency. Just be matter-of-fact about it. Keep the tone brisk and chipper, like you're not even talking about his balding head but rather a pair of shoes that are obviously falling apart. My boy started losing his hair in his early 20s, and I finally had to just insist on shaving it down. He was apprehensive at first but now loves it. Some people just have a hard time visualizing a change in their appearance. Be a friend. Take him to your stylist.

    Liz

    If he is just a friend Dan, then I think you have to keep quiet. If he is just a friend then ask yourself why is this so important to you? Maybe you are fearful of ending up the same way? I think this annoyance is more about your stuff than his in which case I say let go of your fears.

    You know today I watched Cindy Crawford on The View. I actually felt sorry for her. She has had something done to her face (I'm sure for the sake of improvement) and she doesn't look good at all. Can you imagine being CINDY CRAWFORD and thinking you needed to fix your face? What a shame.

    If your friend asks for help with his hair you will be right there because you sound like a wonderful friend. In the meantime just let it go. It's not worth the risk of hurting his feelings.

    johnO

    You really can't say anything unless you have an ALTERNATE plan for him. Telling him he's sexy and needs an update without being able to tell him HOW to update is actually going to be a huge flop. If you're not sure his shaving his head will look good because of the tan/aging thing, then there's really nothing else. The comb-over is probably no worse than the horseshoe.

    If he has the money, hair transplant is great. Otherwise I think you just have to completely avoid the issue. :~(

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