Dating and beauty


When I think of going out on a date, I automatically think of all that entails to get ready for one. It’s the time we women pull out all the stops: shave our legs, wear cute undies that might even match our bra, curl our hair and put on perfect makeup. It has felt like we have to do these things or we won’t be viewed as attractive or put together. Sometimes it feels impossible to separate what we do for the male gaze and what we do for ourselves.


When I was 29, I left New York and moved home to California for 6 months. I stopped wearing makeup. I didn’t feel like I needed to impress anyone and more accurately, I was in a place of wanting to hide. I then moved to upstate New York to manage a hot yoga studio. I was teaching in 100 degree heat so, makeup seemed silly most days and I didn’t wear any then either. I spent 6 months upstate and then returned to the city, moving to Brooklyn and continued wearing zero makeup. I felt weird and really plain. I asked friends if they thought I needed to wear makeup to look pretty or if I was pretty on my own. One of my friends refused to answer (bless her) and kept asking me why I was asking the question and what I thought. I thought I wasn’t pretty “enough” without makeup and pretty soon after started wearing makeup on the daily again. I switched to wearing only all natural brands but, still I felt I needed it. I started dating and felt there was no way I could catch a dude without being properly made up.


I grew up with a tom boy Mom. I think I’ve seen my Mom wear make up maybe 5 times in my life? It’s very rare. She’s beautiful too! She has great skin and I never view her as less than because she doesn’t wear makeup. When I started to go through puberty and wanted to wear makeup, my Mom would tell me over and over I didn’t need it. I had great skin, let it show! She would tell me and I would roll my eyes and apply another layer of mascara. Make up felt cool, grown up and a way to be noticed by the opposite sex. It was also a bonding tool with other girls. I loved “putting on my face” and getting new tools to help the process along. Days when I wouldn’t wear makeup, I would complain I looked like shit and would not want to leave my house for fear of seeing someone. it was a sentiment I heard echoed back from my girlfriends too. A makeup free face left me feeling exposed and vulnerable. We’ve all seen romantic comedies where the heroine either wakes up looking perfect (face full of makeup) or wakes up early to make sure she looks perfect when the dude wakes up. Underneath the make up, I was yearning for perfection because if I wasn’t perfect, I felt I couldn’t be loved.


I’ve spoken at length about how much getting sober helped me. And it really, truly did. It helped me accelerate the self work I was doing and allowed it to actually stick. Getting sober, couple with my self healing journey allowed my self worth and self esteem to grow. I began digging into what I liked versus what I had been told to like or what I was told men liked. I began to question things like Brazilian bikini waxes and shaving my leg hair. I found an internal confidence and felt more and more that I needed less and less external validation. And then I went traveling. I brought my natural makeup as a sort of crutch but upon arriving in Cambodia realized I didn’t need it. It wasn’t because I was trying to hide either! I just felt really beautiful in my skin, just as I was. Somewhere along the way in my healing journey I stopped striving towards perfection. I had worked for a deep confidence and it had grown into me feeling like my face looked pretty great on it’s own. I never even flinched when I met Guy and I was makeup free either. I felt totally myself and carefree. And I haven’t looked back! I still have my natural makeup (that I bought well over a year ago) but, I rarely use it. I love being make up free now. My getting ready routine is pretty quick and thats great but, I really love how confident I feel in my skin. Gone are the days of me anxiously asking friends if I need makeup to look pretty. I feel 10x more beautiful without makeup on than I do with it on now. Even being back in NYC where there can be a pressure to be the most beautiful you can possibly be because there are so many beautiful people here, I feel fucking great. It feels like a revolution. I’m not alone either.

Okay, I feel good makeup free but what about dating? I recently became ready to start dipping my toes back in the dating world. I’m following the protocol I give clients and am using online dating for a month and a half as a tool to practice getting out there, meeting new men, flirting, maintaining my boundaries, passing test, etc. This past weekend I had my first two meet-ups (refresher- I don’t call them dates) and I went totally makeup free. I wore an outfit I would wear normally and didn’t try to look extra sexy or attractive. I was just me! And it felt really liberating. I don’t know if the dudes noticed I wasn’t wearing makeup but what I know they saw is a woman who loves herself and feels confident in her skin, bare skin and all. Finally!

Would you ever go makeup free for a week or on a date?

If you feel like you have to be perfect to be loved, I would love to connect over a session and help free you from that bondage.