How to Find The Confidence To Date Again

One of the things people have asked me most often over the years is: how do I get the confidence to start dating again? Let’s be real, breakups not only can leave your heart battered, they can also be a blow to your confidence and self-esteem. If you’ve been reading this blog for a while, it may seem like I fearlessly go from one relationship or situationship to the next, but that’s far from reality. I rarely blog in real time, so often there’s months between a breakup and when I get the nerve to get back on the proverbial horse.

Getting your dating mojo back doesn’t happen overnight. It’s a journey. Here’s a few things that have helped me over the years.

Heal what needs healing.

Even if it’s been a while since your last relationship ended, there’s always emotional stuff that comes up. In my experience, taking the time to reflect, process and heal these sore spots before you start dating again is never a bad idea. This could involve journalling, making art, taking a personal development course, working with a life coachtalking to a licensed therapist (something I’m a huge proponent of!) or working with another kind of healing professional.

Do things that make you feel good in your body.

I have the tendency to get stuck in my head a lot, so taking time to reconnect with my body is something I try and prioritize (whether I’m dating or not). Confidence is all about how you feel. When I move my body, the endorphins flow and I focus less on how my body looks and more on the cool stuff it can do. Whether it’s running, doing a barre class, yoga, using your favourite sex toys or having an epic bedroom dancing session, find what kind of movement feels good to you & go for it.

Pamper yourself.

I’m also a big fan of getting a beauty treatment (or something done) after a breakup and before re-entering the dating scene. Note: you don’t need to change how you look to be a confident dater, but I find sometimes doing the smallest things (getting a haircut, a pedicure or heck, even a new tattoo or piercing) can give you an extra pep in your step.

For example, I recently had a couple of skin tags removed from the base of my neck. I’ve had them for a while and they’ve always bothered me. But it wasn’t until I was on a date recently and the guy actually tried to pull one off (“hey, you have some fluff on your neck. Let me get that!”) and I had to tell him that “uh, that’s actually attached to my body,” that I decided to have them removed for good. Not only does my neck feel ridiculously smooth now, I also (hope) I’ve helped prevent future awkward moments. Skin tugging = not sexy.

(Sidebar: I used to be very anti cosmetic surgery + treatments, but as I get closer to 40 I’ve become a lot less judgemental. I have several friends who’ve had facial surgeries and cosmetic treatments to reduce the signs of aging & they’re happy, bad-ass women who still very much look like themselves. Next time I’m in LA, I may even swing by Dr. Binder to get an anti-aging treatment of my own. At the end of the day, it’s your body. Do whatever you want for you, not for anyone else).

Update your wardrobe.

When you look good, you feel good. Go through your wardrobe. If it doesn’t fit or you don’t feel good in it, donate it. You don’t need a whole new wardrobe to re-enter the dating scene, but it helps if you have a few pieces that you feel comfortable in. Instead of always scrambling before a date, I like to have one or two go-to date outfits preplanned. For example, my go-to fall/winter look is a black dress, tights, ankle boots and a leather jacket. Done.

Take your time. 

When I first re-entered the dating scene after ending a long term relationship (which involved venturing into the world of dating apps for the first time ever), I mistook “not terrible” for “good.” Figure out how you want to feel in your next relationship (for example, safe, supported, respected). If you don’t feel that way with someone, give yourself permission to walk away.

Be kind to yourself.

RuPaul always says, “If you can’t love yourself, how in the hell are you gonna love somebody else!” And while I do think this is true to a certain extent, I think it fails to acknowledge that self-love is a process. Just because you’re still working on it, doesn’t mean that you’re not deserving of love & respect from the people you date. (I used to think that people treated me poorly because I didn’t love myself enough, but the reality is that some people are just crappy. That’s their problem, not yours. End of story.) You’re worthy of being treated with respect, just the way you are. When you remind yourself of this on a regular basis and cultivate a strong sense of self (regardless of where you are on your self-love journey), rejection doesn’t feel so bad.

Happiness, Yoga and a Good Ass Kicking: All via your Laptop.

I don’t know about you guys but I find it so much more challenging to work-out in the wintertime, especially when you spend most of your winters in frozen Eastern Canada. When I was living in my old neighborhood in Toronto, I adored my local gym which was a 10 minute walk from my house. During the winter I’d brave the snow and walk there several times a week. I thought being in BC where the weather is warmer would mean more frequent gym visits however, I’ve actually been going to the gym less since I’ve been here. To get to my gym here I either have to walk for 30 minutes each way (a work-out on it’s own) or jump in a car. I’d really like to try some of the yoga classes my gym offers but when faced with having to travel there I often choose to just do exercises at home. It’s a conundrum that I’m sure a lot of us experience in the winter.

So, when Gaiam TV contacted me about trying out their new streaming video service I was excited because THIS IS A PRODUCT I COULD ACTUALLY USE RIGHT NOW.

Gaiam TV is the first streaming video subscription service designed to reach people interested in health, wellness,  yoga, fitness and personal development. With over 2,000 titles to choose from it’s basically like Netflix for your mind & body. With Gaiam TV you can access hours of online yoga, pilates and cardio classes plus all kinds of other world class health & wellness programming taught by well known instructors. In other words, it’s pretty rad.

I was worried that the selection might be limited (sort of like how Netflix is for Canadians) however, you can customize the programming to suit your fitness and wellness goals. Gaiam TV offers a “fitness studio” and “yoga studio” which each offer tons of different user friendly options to choose from. Viewers can customize workouts for weight loss, total body sculpting or increased energy and narrow down their options based on level, style, instructor and amount of available time. You can even make playlists based on what you enjoy. The best part? Unlike Netflix, you can watch hours of Gaiam TV without feeling guilty. You might even get a killer six pack out of it.

The best part about the service?




{All images found here}

Gaiam TV’s entire library of videos is available anytime, anywhere, all from the comfort of your computer, iPad or smart-phone. This means you can always work-out at home or take your work-out to go. Maybe it’s the West Coast hippie lifestyle seeping into me, but I like the idea of being able to watch a short relaxation or yoga video on my iPhone whenever I want.

I’ve been trying Gaiam TV for the past few days & I have to say it’s pretty cool. Although the idea of doing Yoga really appealed to me in theory, the videos I actually enjoyed more were the ones that made me sweat. I currently have Jillian Michaels on call, 24hrs a day to kick my ass into shape in time for bathing suit season and I’m loving it. If you don’t want to be yelled at by Jillian until you have buns of steel, there are lots of other famous instructors to choose from (Rodney Yee, Seane Corn, Jillian Michaels, Mari Winsor and Kathryn Budig etc.) There’s even a Reggaeton dance class which I totally plan to shake my white girl “Culo” to tomorrow morning.

If you would also like to give it a try, Gaiam TV wants to offer you guys a Free 10-day Trial, No Strings Attached  so you can see what it’s all about. In case you’re wondering, the regular subscription is $9.95/month for unlimited streaming, commitment free & you can cancel at any time. If I become addicted to Jillian’s yelling (as I’ve heard some people do) and she doesn’t actually manage to kill me with squats & lunges, I might turn into a full time subscriber.

What do you guys think? How do combat the winter work-out blues?

This post was sponsored by Gaiam TV and Single Edition Media. As always on this blog, all opinions are my own. 

Go Easy on Yourself.

One of my favorite people on the internet – Carly from Crowning Venus – posted this video on her blog last week. I know most of you have probably already seen it since it made it’s rounds on Twitter and Facebook but I’m re-blogging it anyways because I love it so much.

Fotoshop by Adobé from Jesse Rosten on Vimeo.

Watching it reminded me that we live in a society full of conflicting messages. Where the “beauty ideal” doesn’t really exist. Where  “Human Barbie Mom”  thinks it’s OK to give her 7 year old daughter gift certificates for stuff like  breast augmentation surgery and mini tummy tuck surgery in her Christmas stocking. Where TV ads for weight loss drugs play during the same commercial break as ads for Burger King. Where magazine headlines encourage us to dissect and hate on other women’s bodies so we can feel better about ourselves (“Worst Celebrity Beach Bodies Ever!”) while at the same time scrutinizing our own (“How to get thinner thighs NOW!”). Love Yourself. Hate Yourself. Eat. Don’t Eat. Consume. Consume. Consume. If this is the background noise to our daily lives, is it really surprising that eating disorders and other mental health issues such depression and anxiety are on the rise?  Everyday we’re fighting a war against the cognitive dissonance  that surrounds us and some of us are literally losing our shit.

Even if you manage to block out most of this negativity there is still a lot of noise to contend with on a daily basis. I’ve grown up as part of what I like to call the “Oprah Generation.” I’m a middle class woman who has had it hammered into her that she should be attune to her own needs, follow her dreams and live the best possible version of her life...because she can. It’s so easy to get caught up in all the self help messages that are out there. Live authentically. Live with Intention. Live in the moment. Affirmations. Goals. Inspiration Boards. Meditate. Juice. Cleanse. Eat meat. Don’t eat Meat. Go Gluten free. Find a spirit animal. Paint your life in crayons to get in touch with your inner child. Have a baby. Don’t have a baby. Be a feminist. These so called “positive messages” can be just as overwhelming as the negative ones. As someone who currently is self employed and spends the majority of their workday online, it’s so easy to get wrapped up in all the amazing, entrepreneurial things the people around me are doing & start thinking: “I’m not working hard enough! I’m not dreaming big enough! I should be doing more!”


It’s all this noise that sometimes distracts me from taking stock of what I’ve accomplished. For example, following the holidays I had a bit of extra “junk in the trunk” that I wanted to lose. I haven’t been going to the gym lately because my joints have been bothering me. Instead, I’ve been eating healthy and going for power walks. Over the past two weeks I’ve walked to and from all my appointments. When I Google mapped it last night I calculated that I have walked 19.6 km this week and close to 40 km over the past two weeks. The Christmas weight is gone, however the other night I had a moment in front of the mirror where I said:

My ass still doesn’t look as good as it did when I was working out at the gym 4 times a week”

That’s fucked up.

I’ve walked the equivalent of a marathon this month.

Once I allowed this information to sink in, I took a cue from Carly and decided to cut myself some slack and focus on the things I have accomplished:

This week I’ve blogged. I’ve written for Canadian Living. I’ve written for Elle. I’ve gone to counseling. I’ve gone to the dentist. I’ve seen my friends. I’ve read. I’ve eaten well. I’ve booked a trip to Vegas (!!!!!) I’ve walked the equivalent of a freaking half marathon. I’ve done all of this even though my heart feels completely tattered and hanging by a thread. I’ve pushed through.

I’m proud of myself. Why is that so hard to admit?

If you’ve ever felt like this too, here is my proposition: Let’s be kinder to ourselves. Celebrate what we like about ourselves. Celebrate the big accomplishments but also the baby steps. Leave the negativity to the haters. Let’s go easy on ourselves.

Here’s to being imperfect & fabulous!

Happy Weekend! xo


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