The Long and Short of It: Wigs and Dating (as if dating after 40 isn’t complicated enough….) by Kerry

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Hi everyone! Kerry here (that’s me bald and then wearing Brittaney by Envy in Creamed Coffee) and I wanted to share my story on dating and what I have learned in the 5 years I have been wearing wigs. Because while we all have different experiences, maybe my story can help someone.

Let me start by saying that I have had hair loss since my early teens and was married without the Victorian intricate updo of hair that I had dreamed of at the age of 21.  I made do though, and I was happy.  My new husband had been going bald early, too – so we had that in common. It was annoying and there was some shame and wistfulness for a full head of hair, for longer hair, for anything but what I had, but I was focused on ignoring it and it didn’t really seem to matter.  We divorced in 2012 because we just grew apart – we are still very good friends to this day and are  focused on raising our daughter.

So, that being said, I was still deep in denial of my hair loss and busy living my life. I met Rich in 2012 – way early to be dating after my divorce, but we did nonetheless. My hair was never a problem – even my crazy bedhead in the morning (my hair was thin and oily, so yeah – crazy bedhead!).  We were in love and he thought it was cute – something only someone in love could ever say, lol.  It was a quick 6 months and our flame burned fast and bright.  For complicated reasons, we broke up. I was beyond devastated. But that’s not the end of that story….

Flash forward a year and I’m in a different state, at a new job in a new industry, thinner and happier than I have ever been in my life and finally ready to look for love again. I start a dating profile. This is me au natural in the boxing gloves – I would blow dry and fluff what little hair I had and let the comments from hairstylists asking me if I had tried this hair loss solution or that one roll like water off a duck’s back. I had ignored it for this long, I was good at it!

And I wasn’t going to let that or anything else stop me. After all, I have enough personality and smarts to make up for the hair or whatever other physical deficiencies I have – I just needed someone to give me enough of a chance to get to know me and they would see past it all.

Then I met Shane. Shane was a lot of fun – a truck driver and a funny guy. He loved to talk, and we connected over the phone immediately. The first time we met, sparks flew. He was outgoing and sweet, very big on social media announcing our relationship and our dates to his friends on Facebook. It was a lot of fun! We took this picture about 5 weeks in because he wanted to post our first couple picture for his friends. It was the only couple photo we would take. He texted me from on the road and explained that he didn’t want to post it because you could see how little hair I had. A really rough phone call later and he had me convinced I needed a wig. I didn’t know where I was going to get one. I didn’t know how I was going to afford one. I didn’t know anything other than all that shame and fear I had been suppressing was now overwhelming. I needed to figure this out, to escape the pain and embarrassment I thought I was keeping well-hidden for so long. Long story short, that is how I found Heather and Cysterwigs – as so many others have. I found a resource and more importantly a truly relatable, straight-forward woman close to my age wearing wigs! I bought my first wig from Cysterwigs – on Heather’s suggestion I got Jamison by Estetica in a color close to my natural hair color, R2/4. I announced it on Facebook – “I wear wigs now, so expect me to have a good hair day every day!”

Shane never saw me in a wig – we broke up soon after that phone call about my hair, but for other reasons. He had served his purpose in my life and left quietly, thank goodness.

About a month later, back in the online dating game, I met Stephen. This was the first guy I would be dating that I would have to “reveal” my secret to. I didn’t know how to handle it. I decided to wait and didn’t mention it while we talked or during our first date, which despite us both being awkward, went pretty well! Texting a few days later, Stephen gave me an opening and with my heart pounding in my ears (I really liked him!) and my coworkers and boss egging me on, I told him. I guess it was a big moment for me because I saved (most of) the conversation:

I was overjoyed. He was cool with it. We continued to date for almost 2 years. In all of that time, he saw me without a wig once for just a moment, a few weeks into our relationship. He said he had thought I had less hair than what I did have and that was about it. I was so ashamed and embarrassed that I had walked around half bald for so long, here was the first person who had never known me like that and I didn’t want to lose him. So I had a cheap “sleeping” wig that I wore on nights spent over. I was happy…for a little while at least.

About a year and a half into the relationship we had a discussion – he thought I should show him my head (I had started shaving my hair off at this point) because it would be better to do it on purpose than full of shame and when I am sick or some other necessity. I thought about it for a week and decided he was right. He was spending the night at my place and I told him I was going to sleep without my hair for the first time, that I would come out of the bathroom and let him see. I wanted him to be prepared. I took my wig off and left it on the counter and came out. No expression, no real reaction. He was just OK with it. We went to bed and I tried to be cool. He turned away from me and feel asleep with his back to me. It felt like rejection. I quietly slipped out of bed and put my wig back on, never revealing my bald head to him again. We broke up months later for other reasons, but really – that was the beginning of the end.

I dated a few people after Stephen. I had different wigs on in my online profile pictures, but what women doesn’t change her hair? I felt like it was an M. Night Shyamalan movie – all the clues were there from the beginning. I revealed to one guy I had dated (my new rule was to wait until the third date) that I wore wigs. He seemed a little shocked but OK with it. He then brought it up at our next date, saying “I said I was OK with you wearing wigs, but now I’m not so sure.” It made me mad. I responded, “Well, since I’m the one wearing them and I’m OK with them, I don’t see why the hell you wouldn’t be!” Why should I have to make him feel better? We ended up being friends for a while, but honestly – he was a selfish person. When someone shows you who they are – believe them.

So, remember Rich? (He’s the one holding the giant hammer, lol). The one I dated too soon after my divorce and who loved my bedhead? Well, I really never stopped talking to him. We kept in touch for those 6 years we were apart, each dating other people, but never really letting go I suppose. I moved back and after almost a year of not talking (we got in a fight about something stupid, as most fights are) I reached out to him. Those complicated reasons we had broken up over were now in the past, and I was a new woman. I was well out of my divorce, used to being on my own, I had lost weight, found wigs, found my independence. My hair never mattered to him and it still doesn’t. He is one of the few people in my life that I feel perfectly natural having a conversation with, being around, just being me – without a wig on. Why? Because unlike Stephen who tried to feign that it didn’t matter, it really doesn’t to Rich. He loves me with all my faults. He shows me off to all of his friends at work and thinks I look great in every wig. I can breathe around him. Relax.

Does that mean we are meant to be – that this is my fairytale ending? Probably not. Life doesn’t work that way. But, I have had a good selection of relationships and I know what feels right now – how it should be. I should feel comfortable with my partner – hair or not. Because it really doesn’t matter. What does matter is that we get along, whether we have similar life goals and good conversations, that we have fun together, that we are best friends. We have enough in common to relate to each other and enough different to keep it interesting. Hair doesn’t really figure into any of that.

I am glad for Shane coming into my life and pointing me in a new direction. And I am glad he left soon after. I am sad that things didn’t work out with Stephen, but that memory of him falling asleep with his back to me makes me even sadder. I wish I had found that out earlier in the relationship. If I do end up dating again, I think I will just put it in my profile – a small blurb that reads, “Oh and I wear wigs – so expect me to have a good hair day every day.” 😊

You can see all of Kerry’s guest blogger posts here.



  1. June 6, 2018 / 5:02 pm

    Thin and oily hair? Hair loss during adolescence? Sounds familiar … Your story is very touching and HEROIC, Kerry. All our stories are different but they are equally painful and eventually, they bring us to a state of wisdom. I “came out” about my hair loss because of courage I found by watching Heather, and by seeing you in your posts and pictures, and by learning about all the other ladies in our community. But just prior to my coming out I had a hair loss related panic episode that drove me to the hospital. Such type of anxiety isn’t warranted … not over hair. Thank you for the invaluable support! You are wise and are on the right track. Keep punching!!! (BTW I loved that plum colour on you!!!)

    • Kerry
      June 13, 2018 / 1:51 am

      Hi Anne!

      Thanks so much for the kind words. I’m not a hero, but I do try my best to be brave – especially when I don’t feel like it on the inside. I’m just glad to be able to help others going through the same thing – we all feel so alone when it is happening, and I think once we feel we aren’t, that is when we are really strong.

  2. June 6, 2018 / 5:04 pm

    Thanks for sharing! You are a fierce and spectacular woman of substance!!!!!! Some day your prince will come. Your confidence will attract wonderful people into your life.

    • Kerry
      June 13, 2018 / 1:53 am

      I hope so! Thanks so much for the amazing compliment, Mel! I’m going to keep looking – you have to put yourself out there and I want women to know that just because you lose your hair doesn’t mean this part of your life is over.

  3. Cynthia Lewman
    June 6, 2018 / 6:14 pm

    Wow, Kerry! This is so honest and true. Even though I hardly know you but through a few business email exchanges, I knew you were a straight up, genuine honest, loving and beautiful woman. This just confirmed it. Your story is so raw and real. I love you for that. The main reason that I shop at Cysterwigs (other than the FAB promos and easy returns!) is the PEOPLE. I knew in my heart that Heather would surround herself with people who are as beautiful and wonderful as she is. Thank you for writing this. Thank you to all of you at Cysterwigs. I love you all!

    • Kerry
      June 13, 2018 / 1:54 am

      Thanks, Cynthia! I really admire Heather and your words really mean a lot to me. I’m happy to bare pretty much all in the name of making at least one other person not feel alone. Writing this was a cathartic experience and seeing everyone’s comments makes it that much more wonderful 🙂

  4. Sheree
    June 6, 2018 / 8:30 pm

    Kerry! I love, love, love your story! It’s not easy to be so personal and vulnerable on social media, so a big kudos to you for your honesty, as well as your excellent and relatable writing style. You’ve had such a variety of experiences with men. Wow, I’m sorry some of these guys have been such a disappointment. Based on everything I’ve read of yours on Cysterwigs in the past year, you are a lovely person. You’ll find the right guy; he’s out there somewhere. It just takes a while sometimes. As my close friends and I used to say to one another as consolation anytime we experienced a break-up or bad experience with a guy, “Awww, [insert man’s name] doesn’t deserve you, sweetie! If I was a man, I would totally date you; you’re marvelous!” It always made us laugh. So, to you, Kerry, I say, “awww, honey, forgot those guys. You’ll find another one. And I would totally date you if I were a man!”

    Here’s a quick story before I shut my computer and get ready for my son’s high school graduation tonight! So … I just began wearing wigs about a year ago (after my 10+ years of online dating, after a 12 year marriage). I’ve been fortunate; the only man I’ve had to “deal with” regarding my hair loss and wigs is my sweet boyfriend of 5 years. When I began experimenting with wigs, it really freaked him out at first because he is a person who does NOT handle change well. It’s just the way he is, in spite of all my efforts to introduce him to variety and spice in life. Amazingly, he’ll now willingly dine at Indian and Vietnamese restaurants with me – yay! But that’s a different story for another time. Anyway, after 6 months or so of encountering me each day with a new hairstyle and color, he has finally chilled out. In fact, he’s now very supportive and complimentary of my plethora of styles and looks. And, even though it took him a long time to warm up to the idea of me in wigs, he never, ever made me feel ashamed of my thinning hair.

    I feel very fortunate to have such an understanding partner. I know lots of men (and women) who judge us wig-wearing folks, likely because they have no hair loss themselves (yet!). For that reason, I’ve made it a habit to announce to anyone who compliments my hair that I’m wearing a wig. Sometimes it sparks a conversation and hopefully becomes the impetus for compassion and acceptance of women with hair loss. Just trying to change the world’s attitude about Women in Wigs, one person at a time!

    My apologies for any typos or grammatical errors! OK, shutting down the computer so I can shower, plop on a wig, and run out the door to my baby boy’s graduation. Have a wonderful day, my fellow wig wearers! <3

    • Kerry
      June 13, 2018 / 2:00 am

      Hi Sheree!

      Hear! Hear! I am right there with you – I tell people I’m wearing a wig because I want to fight the stigma. That’s awesome that your boyfriend is opening up – I think that is really cool that he is willing to soften a bit for you. I hope you had a great time at your son’s graduation – such a huge milestone! Congratulations to him 😀 and thank you so much for the support and sharing your story, too!

  5. Janel
    June 6, 2018 / 8:38 pm

    What a courageous post! Thank you for sharing. You are beautiful inside and out and I love your many looks! It’s great to always have a perfect hair day, isn’t it? Love and hugs to you!

    • Kerry
      June 13, 2018 / 1:47 am

      Thanks, Janel! I’m so glad I shared!

  6. Kathleen Ryan
    June 6, 2018 / 11:05 pm

    Hi Kerry..awe I so enjoyed reading anout your hair and dating journey…I love the place you are in now..oh I wear wigs..good hair day that…:-) xxoxo

    • Kerry
      June 13, 2018 / 1:46 am

      Thanks, Kathleen! It is definitely a journey.

  7. Zanetta
    June 7, 2018 / 12:22 am

    Kerry, you bravely address so much in this post. I love the part of “if you’re good with your hair why do you need to worry about how he feels”?
    No need to dance around someone else. Coping with hair loss makes you strong, you can’t be wimpy and survive.

    My favorite line: “Oh and I wear wigs – so expect me to have a good hair day every day.” 😊 Yeah!

    A beautiful girl at church asked me about my hair so I told her it was a wig and I was tired of trying to fix the thinness. So, when it rains and the humidity is off the charts, I’ll have awesome hair.
    Her response was, “I’m jealous”.

    • Kerry
      June 13, 2018 / 1:45 am

      That’s great, Zanetta! I have found that same response from many women – they want to know where I get my hair done and they are amazed that not only is it a wig, but it doesn’t cost thousands of dollars. -Kerry 🙂

  8. Kelly Easterling-Van Sickle
    June 9, 2018 / 10:55 pm


    Awe! Big Hugs! Thank you SO much for sharing your story! You know we get these questions once in a while in the CCHD and being able to share your store will help so many!

    I met my husband when my hair was thinning and then went through the wig-wearing process with him. When he and I separated, it was my first jolt into the dating scene and my first time having to have the conversation with new folks about my wigs!

    Ironically, one of the men I dated during that time, was my old college sweetheart, who was embarassed to take me around his friends decades ago, because of my ‘balding head’. But when he saw me, thin and with long flowing locks, um…. let’s just say, Karma can be SO sweet when it isn’t occurring to you! LOL He oogled and pursued me….but that too, was never meant to be.

    During that dating period, I just ripped the band-aid off and told the men upfront because I was so nervous they would feel the wefting or wig cap if they touched my head or tried to kiss me. LOL All that anxiety stressed me out, so I just began saying, hey, “I have an auto-immume disorder, I am bald and I wear wigs” –if that is an issue for you, we can end things now. Most could have cared less, and the man I ended up dating and falling in love with was bald too, so that was never an issue. Just as you experienced, those that had an issue with it, were really not the ones for me anyway. I believe my higher power has a way taking care of things for me! 🙂

    I know wig-wearing is scary and unatural in the beginning, but once you get comfortable in your own skin, and find styles and colors that work for you it can be SO liberating, not to mention, a HUGE time-saver getting ready! I have learned to embrace my journey of faux hair, and just have fun with it. I mean, hair is just another accessory so accessorize away!

    I am so thankful for Heather, the family and the opportunity to work with such a fantastic team! Together I know we can burst through this stigma of wig-wearing and make it the ‘norm”!

    • Kerry
      June 13, 2018 / 1:46 am

      Heck yes! We are the pioneers 😉

  9. Holly K.
    July 6, 2018 / 1:02 pm

    I loved your story! It struck me that you are beautiful on the outside and you are just as beautiful on the inside! You are such an inspiration to all of us, thank you so much for sharing your story.


  10. MelMel
    April 14, 2019 / 2:34 am

    I’m grateful for your story. Thanks for sharing. And, the comments helped me too. I told a guy I had gone out with 3 times about my wearing wigs and he didn’t call me again. It hurt, but not too badly because I knew if it was an issue I don’t need to be hanging out with him anyways. But he always tried to touch my hair and I would be all freaked out about it and he noticed my behavior but not that I had a wig on. Anyways. I recently started wearing totally different ones on different days because I’m working on not caring about what anyone thinks anymore.

    • Gina
      April 14, 2019 / 6:33 pm

      It is a process MelMel! I know it takes some time getting use to and allowing yourself that freedom. I hope the transition comes fast for you.

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