Should You Cut In The Awkward Stage?

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The most common question we’ve gotten in the history of time has been, “should I cut in the awkward stage?”

In our definitive post on The Uncomfortable Truth About Awkward Stage Hair, there are dozens of variations to this question, from should I cut in the awkward stage, should I trim the sides, should I use product...WHAT SHOULD I DO?

Jason helps us determine whether you should cut in the awkward stage.

It’s a fair question. Most guys going through the awkward stage are stumbling through for the first time. Many have been there before but never made it. Still others are back in it after donating their hair to charity and hitting reset.

Whatever the case, it’s unstable ground. As you can read in the comments on that post, our answers to “should I cut in the awkward stage” have mostly focused on trimming around the ears and the back of the neck, but generally to let the rest keep growing.

Sound advice that has served us and others well. Still, we wanted to dive deeper, so we set out to find more concrete answers to whether or not you should cut in the awkward stage. And this time we called on our favorite hair pro and paid a visit to House of Imago Salon in San Diego.

To help us get to the bottom of things, we were lucky enough to enlist the services of three courageous young men in different phases of the awkward stage: the early going, the mid thick of it, and tail-end awkward stage.

Not only did we get real-life awkward stage guys, but each being in different phases gave us a great mix of lengths and hair situations to address. Because we quickly learned there may be different approaches to different phases of awkward—and certainly to different types of hair.

Should you cut in the awkward stage? Shayna is explaining with Billy's hair.

With Jason, Skyler and Billy, we sought the wisdom of Shayna at House of Imago. We started off by asking each guy to tell us what was going on with his hair, how he got there, and what he was trying to accomplish. Once in the chair, Shayna provided in-depth analysis of what she was seeing with each man’s mane and her strategy for approaching.

The main goal: help these guys’ hair look good (or at least ok) while they are growing it out. And you can be the judge, but the guys agree: the results speak for themselves.


So, should you cut in the awkward stage?

The short answer is yes. It will be a different type of cut depending on your hair type, where you’re at and where you’re trying to be, but generally there is a good trimming strategy for most guys suffering with awkward stage hair.

Skyler putting his locks on the line to answer whether you should cut in the awkward stage.

Now it’s your turn.

After watching you should have a good sense of where you stand, and how you might wish to proceed as you navigate through your own awkward stage journey.

Armed with real-life examples and seeing how it’s played out with our fearless volunteers, you can prepare for your own visit to a hair professional, including what you should actually say when you walk in there, detailed further in our post, Confidently Navigate Your Visit to the Salon.

After the big day, one of our spirited volunteer brethren wrote us a follow-up note he wanted to share with all the awkward stage hair guys out there:

So here's the thing, guys:

Whether you have short hair, long hair, or awkward hair, it really comes down to confidence. Not over-confidence. Just confidence.

Maybe your hair is on point, or maybe it's a glorious mess. Either way, your hair is an expression of you, it isn't you.

So just be who you are. If you feel uncomfortable in your own skin, then that's how others will perceive you.

If you have confidence, then people will feel that and follow it.

I guess what I'm saying is this:

The best way to get through the awkward phase it to just own it. Mold, leave it, laugh at it. In any case, your hair may be awkward, but you are still awesome.


Big thanks to Jason, Skyler and Billy for volunteering, showing up and putting their locks on the line for the greater good of humanity. We hope their bravery helps you power through the awkward stage with courage and commitment.

There's an enormous volume of additional awkward stage hair content right over here.

Last but not least, special thanks to Shayna, if you’re looking for a hair pro in San Diego, give her a ring at House of Imago.

Keep lettin’ it ride man. We’ll see ya on the other side.


What other questions do you have about awkward stage hair? Any tips you’d like to share? Don’t keep them to yourself man. Comment below.


  1. I have been growing my hair for 3 years. I have had two trims; about 2 inches each time to even it out. I have fine hair but a full head of hair at age 60 (not as thick as when I was younger). Since it is fine hair, it is not as thick as desired. My hair grows faster in the back than the sides and front. I am going for my third trim in the next week. What are you trim suggestions so I can keep as much length as possible but my hair look fuller and thicker. Any product use suggestions to make it look thicker in the back as I have all your products. I really enjoy your products, tips and blog.

  2. Hello. Ive been growing my hair for about a year and a half. Its about ten inches I’d say. I read that having it tied up in a bun or pony tail too often stunts the growth and is unhealthy for the hair, making it break. So i stopped tying it up. The problem then was, not thinking while i was trimming my burns and beard, I went up with the trimmer and trimmed the longer hairs above the sideburn and over the ear. Now that hair is three inches while the rest is 10 inches. When i do put it in a bum now, those hairs flair up and it looks like shit. I want to get to about 18 inches, maybe a bit less… just let those short hairs grow Or should i just trim them consistently? If i let them be, is there a way to stop them flairing out while in a ponytail? Dumb mistake. I must not have had my voffee when i trimmed the other day.

    1. Author

      A most fascinating predicament, Dominick, though concerning. I am visualizing this in my mind and it’s a real sight.

      Thing is, if you trim it again you’re gonna have to keep trimming it forever. Some guys do this, a couple who come to mind are Clay Mathews and David Bakhtiari. If you go that route, I would go to a salon or barber shop next time so at least they’ll get you all straightened up.

      If you’re already at three inches on the sides you might as well keep lettin’ it ride. It won’t be too much longer before it starts blending with the rest of your hair. As it gets closer you might trim the top a small bit to even things out. Either way you might seek professional help with this one.

      Check out my recent post about growing out my neck hair, you’ll find some similarities.

  3. Yo you sexy long lock brothers! I’ve been growing my hair out for about 4-5 months and I’m terrified of split ends. When would you recommend a trim for the first time and how much should I trim it? Also, after I trim it how long should I wait until trimming it again? Thank you for educating us young long lock pupils with your knowledge.

  4. Hello! I was attempting to grow my hair before but got discouraged since the top was wayyy longer than the sides. I took advantage of quarantine to cut all of my hair to the same length. I didn’t cut it completely on any part of my head, i just brought all of it down to the same height. With that being said, I now have fuzz about half an inch to an inch in length all over my head, and since I didn’t touch the back, it’s almost starting to look like a mullet, but like a really short mullet. Should I trim the back so that it’s a square cause rn my hair looks like trash from the side.

    1. Author

      I wouldn’t. You’re just gonna have to wait it out man.

  5. Yo! Been growing my hair for 11 months now no trim whatsoever. Almost have it as long as it was in high school (just below my shoulders) but I’ve taken much better care of it this time. My question is – if I just let it ride all the way through, will I still need to get it cleaned up once I pass the awkward trials? I lucked out with fine and slightly wavy hair but I’m still getting a big poof surrounding my ears and the back is flipping up and out lol. I’m owning it now but don’t want to still look awkward with a flowing mane for not getting a trim now…as nervous as it makes me. Can’t trust just anyone with the locks.

  6. I just started growing my hairout, but its starting to look more like a boelcut than anything else. Should I just let it grow until it’s at the length I like or get it trimmed??

    1. Let it ride Finn! As it gets longer you could get a slight variation to give it some better shape. Much like Shana provided for these guys.

  7. Tips for getting through some awkward stages by yourself (sans stylets, with your own clippers & scissors) would be great.

    I’ve always cut and maintained my own long hair. After a recent buzz cut, I’m trying to grow it back out & finding stuff on self maintenance is difficult.

    1. Author

      Yo Tam, thanks for the comment! Will get this in the queue, glad to have you here!

  8. Hi there, looking for some advice. I have very thick dark tight curly hair and for 2 years i had long hair (chin length when curly, longer when straight) on the top of my head, and a shaved undercut back and sides. Think 90s Jason Newsted.
    I shaved it all off last july to raise money for charity and so i could begin to grow a full head of hair as I wasn’t satisfied with a smaller amount on the top of my head. However i gave up in October as i thought I looked ridiculous with the mini afro growing on my head. I shaved the back on sides and grew out the top. I last got the sides and back shaved in May, and since then i have been growing all my hair out. It is a shorter length at the sides than the top and as i had most strands on the top of my hair dyed a light blonde it’s quite noticeable that the sides aren’t. What should i do now?

  9. Hi there, looking for some advice. I have very thick dark tight curly hair and for 2 years i had long hair (chin length when curly, longer when straight) on the top of my head, and a shaved undercut back and sides. Think 90s Jason Newsted.
    I shaved it all off last july to raise money for charity and so i could begin to grow a full head of hair as I wasn’t satisfied with a smaller amount on the top of my head. However i gave up in October as i thought I looked ridiculous with the mini afro growing on my head. I shaved the back on sides and grew out the top. I last got the sides and back shaved in May, and since then i have been growing all my hair out. It is a shorter length at the sides than the top and as i had most strands on the top of my hair dyed a light blonde it’s quite noticeable that the sides aren’t. Where should I go from here?

  10. So I have never tried to grow out my hair until recently, I’m 15 and I’ve started growing my hair out for around 5 or 6 months now and I’m trying to grow my hair out to my shoulders, a few problems I have had with my hair during the awkward stage are:

    I have hair that is thick and the sides of my hair are curly so I find it difficult to style it.

    The back and sides of my neck look horrible due to my hair sticking out and I’m not sure if I should cut it or not to make it look more presentable.

    Since I grow out my hair some of my friends have said that I shouldn’t because I will look more like a girl and to just cut it and I find it so demoralizing and I’m not sure what to say to them.

    So my questions are, should I cut the sides and if so how much should I cut off to make my hair look better, is there any way to style it and should I even try growing my hair out at my age since I worry that it might make me look more like a women rather than a man?(I know the last question might sound stupid but that question has been in the back of my mind for a while now).

    Thanks Guys.

    1. Author

      Yo Daniel! Glad to have you here man, and thanks for your questions.

      I would be cautious about cutting too much on the sides; it’s a slippery slope, before you know it you’ll be square back in the awkward stage.

      Get a little trim around the sides just to clean it up, maybe the back of your neck too.

      In the end, you have to make it through the awkward stage, there is no getting around it. But it’ll be worth it.

      Tell your friends they are bogus and you’re letting it ride. It’s ok to be different, what should everyone run around with the same haircut? Hell no. You can always tell them you are growing it out for the next Great Cut:

  11. So I have tried to grow out my hair many times but failed every time due to the “awkward stage”. A few problems I had personally that I couldn’t get over:

    I have super thick and curly hair which made that awkward stage appear even worse, almost puffy Afro like.

    My neck hair is brutal. I need a weekly neck shaving to clean up and look professional for my job.

    My questions are, is there a specific way to cut thicker hair during this process to not make it look as “poofy” and how do you recommend cleaning my neck hair while trying to grow it out and at the same time trying to maintain a “clean and professional” look for my job?

    Going for that Bradley Cooper Star is Born look!

    1. Author

      Yo Stephen!

      Thanks for writing in man. Like you, I failed many times before finally making it to the promised land—though lucky for me, I never had to deal with the “poof.” Even so I can understand your pain.

      I do have the neck hair thing. I have a set of small clippers and I’ve gotten to a point where I can usually do it myself, or I’ll ask a distant acquaintance do get in there for me. In any case just don’t get too close to the long stuff, I suggest keeping a thin line of shorter hair acting as a barrier around the hairline so as not to accidentally trim the long stuff.

      The curly hair: bigger challenge. For one thing, definitely keep it cleaned up around the ears and neck. As for cutting it for thinning purposes…I’d hesitant to experiment with scissors. I think you’ll be better off trying products designed to decrease frizz, which will hopefully dampen that poof affect. Diva Curl is one. Also check out this post or this post.

      Let us see if we can dig up any more on this topic. If you’re in SD I can recommend someone. Hope this is at least a little helpful.

  12. Hi gentleman. Been in the journey of growing out my hair for 5 month & 8 days for now . It’s been a journey of messed hair & dilemma on cutting the hair or to keep it and im happy with the hair growth for now. Slicked back style for business & tied ponytail for casual kinda style , it is a variety of style available to every people who’s growing out their mane. Until then, be strong gentleman.

  13. Finally going for it. Have tempted a couple times before to go Long and failed. Thanks to a few inspirational dudes and my wife showing me some love I’m committed. Question I have is do you keep cleaning up around the ears and neck till its obvious your growing it long? I’m 2 months in. Thanks guys!

  14. Only two months in but looking forward to the journey. Great article and will be visiting regularly.

  15. I’ve been growing my hair for 4 months now should I go and trim the split ends what is your guys recommendation

    1. Author

      Yo Tanner!

      Most guys don’t have split ends after four months of growth, but it wouldn’t hurt to get a clean-up trim if it’s starting to look messy. Make sure to tell your hair professional you are growing it out and you want to keep the length.

  16. I’ve been wanting to let my hair grow for a few years and yes, I couldn’t get past the awkward stage. This time I googled pics of men with long hair for inspiration and stumbled upon The Longhairs videos and web site. This isn’t just a product sales web site…it’s more of a support group. Styling and care tips for longhairs and encouragement and hope for us shorthairs. So with this new-found support, I’m doing it this time! It’s really hard to go get that trim when you want your hair to grow longer, but I did it yesterday. My opinion – yes, get that trim. With short hair I can say that every time you get your hair cut it feels good. All those uneven hairs back under control. This time I told the stylist that I want to grow it out and to only cut enough to get it in shape. After the trim, my hair feels so much better; my fingers, comb, and brush glide through my hair much easier. I don’t think longhairs can understand how your hair can “feel” good after a cut but I think shorthairs will realize that it’s not just an awkward “look” that’s bothersome, it’s that awkward “feel” that gets on your nerves. Also if you’re going from “Businessman side-part” cut like I am, when it starts to get long your hair is totally the wrong shape when it grows out. You need to trim it into the right shape for length. After watching the Longhairs videos, I also realized that I’m not leaving work on Friday with a crew cut and coming back to work on Monday with El Rubio hair, which would shock everyone I know. If you’re worried about how others will feel about your long hair, you have to realize that everyone you know is going on the same journey with you. The transformation from short to long hair takes time and your acquaintances will gradually adjust to your long hair along with you. I think getting regular trims along the way to keep it looking and feeling good as it grows will help me beat the awkward stage.

    I grew up being told that men/boys with long hair look like a sissy or girly. Ironically, men with long hair look more masculine. Now that I’ve found The Longhairs site, I understand that it takes masculine courage and determination to let your hair grow out. Thank you guys for not just selling your products but for also providing this great support forum.

    1. MIKE!! Such a good comment man, so stoked you found us and thanks for sharing. Totally agree with everything you said here. I wish you continued success on your journey and we’ll see you around the blog.

  17. It’s difficult to commit to growing out your hair, only to be confronted with an uneven do for months on end. On the one hand, it would be an easy decision and go get a haircut. For me though, I simply reminded myself of what long hair was like for me years ago and the fun of having style options every day based on mood. I pulled it all back, waited it out and eventually reaped the reward of long, beautiful locks. I switch around between styles, but for me, the most useful and best looking is a half-up/half-down style using a cool Hair Ties For Guys elastic on a small pony in back. (It’s also best for summer top-down driving.) I have received countless positive commentsabout my hair from women, but the half-up always brings the greatest compliments. My best advice to someone enduring the awkward grow-out stage is to just recommit to the ultimate result and tough it out by pulling it back for now. Best of luck, guys!

  18. to avoid cutting during the akward stage, and to can more quickly tie your mane in a low ponytail, you must first prepare your growing out
    the first subject did begin from a buzzed cut, and now his hair is much layered and thin in the lenght; in that case, it’s better cutting around at the hairline until all the hair come to that lenght; after, the akward stage will take less time ( 10-12 monthes to tie the hair)
    if you slick back the sides during the growth if you want avoid the mullet, you can trim the back, but avoid a shorter back bob ( you must have a little length on the back to tie the hair) ; it was the case of the second subject
    if you accept a mullet ( to wear a high ball) , it will more neat if it’s trimmed straight ( third case)
    when you begin from a pompadour, as the lenght of it give a fringe to the eye brushes, you can begin growing out and you trim at the hairline until all the hair come to this lenght, then you grow out
    congratulations to Shayna who is parsimonious with the scissors !!! too stylists does’nt accept their customers wear longhair…( and cut for making last the akward stage and discourage the subjet to grow out !!!)
    i’ ve shared that video and some explanations in french language :

  19. Dudes. This is exactly what I needed. My mane is getting unruly and it’s time to tame it a bit. Just the information and inspiration I needed this week. Thank you!

  20. Great watch….. all those cuts worked great on all 3. Now they can move on and grow it out….that woman cutting knew her stuff. Need a blue winter cap they coming in again… keep it long and strong

  21. This is a fantastic vid…very informative with good solutions for each guy. The hairstylist knows what she’s doing, and she’s not trying to cut off three inches of hair like some hairdressers do! Great job!

  22. I slicked it back with pomade and kept cutting the back until it was pretty even so I wouldn’t have a mullet, then tied it back and used pins to keep anything sticking out from flying away.

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