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.

Latest pins

Follow on Pinterest