Ladies: I’m a divorced professional stylist who won the online dating game. Here’s how you can, too.

Thinking about dating after being married for years can be intimidating, exciting, and frankly, straight-up terrifying. When my marriage ended I was (I thought) eager to start dating and I set up a dating profile almost immediately. But when the day finally came – my first date in almost 17 years – I was filled with anxiety. 

What if I have nothing to talk about?

What if I do something embarrassing, like trip on my way to the table? 

What if he tries to KISS ME??!!

I almost backed out. But a pep talk from an amazing friend and some straight up GIRLPOWER music (thank you, Rhianna and Beyonce and my two daughters who introduced me to their music!) and a pair of new IRO jeans that my best friend convinced me I needed for my new dating life (she was right) – I somehow made it through the date, with my self-esteem in tact.

Since that day, I’ve spent a LOT of time preparing for dates. My friends teased that it became my hobby (they weren’t entirely wrong!). Over the course of a few years, I honed my craft and actually began to truly enjoy it – to thrill in it, even. I realized that there were a lot of things I could apply to dating from my day job as a stylist. Like a chess game, once you have a few good strategies (and a few outfits that make you feel amazing) in place, you can begin to feel confident enough to take a few risks. 

Here six of the top tips I give to my clients and friends embarking on this journey: 

  1. Start with the fundamentals. Address your foundational pieces. Chances are you are wearing a yellowed bra that is old, stretched-out or otherwise ill-fitting! Go to a good lingerie shop and have the saleswoman help you find a bra that actually fits AND looks good. You will feel sexier and empowered just knowing you have it on.
  2. Keep it easy. The day or evening of a first date is not the time to reinvent the wheel. Create a date “uniform” where you have (for example), great fitting jeans, a comfortable pair of boots (see below), your fab new fundamentals, and just swap out different tops. 
  3. Treat yourself to one new thing: a perfect pair of jeans, a new great pair of boots (with a little lift of heel to make you feel taller), a new haircut, or even some highlights. One key element of getting through your first date (and so many more) is feeling good about yourself because, after all, self-confidence is attractive. “Look good, feel good” is an old saying that still holds true. If you feel like you look great you will feel great and more confident. 
  4. Accessorize: most first dates are sitting next to or across from someone, so what your date will see most of is your top and jewelry. Either a simple top and some favorite jewelry or an interesting top and minimal accessories are great choices. 
  5. Never show up on a date in shoes you can’t walk in! You’ll want to feel comfortable enough to take a leisurely stroll or head on to a new adventure should your date take on a life of its own. But obviously you want to feel good in them (i.e. sexy) so while it’s good to strike a balance between cute and functional, leave the “sensible” shoes at the office.
  6. HAVE FUN. This is not a styling tip, just a life tip. Seriously. This should be a fun experience! This time around, you’re not a twentysomething full of insecurities. You’re not (necessarily) looking for a life partner. You can use this opportunity to learn more about yourself and who you want to spend time with. You can try new things: go to concerts, try new foods, visit a neighborhood you’ve never explored, and open your mind to exciting opportunities. 

After a few months, the most important thing I learned is that I wasn’t “just a wife and mother.” I rediscovered my femininity and also my sexuality (another blog post entirely!). I had a client tell me after working with me say, “I would walk down the street and feel invisible, and now I feel a new vitality that was dormant for so long. I forgot what it felt like.” I definitely related to that comment and know many other women who have said similar things. My advice is to try not to overthink it, and just enjoy your newfound freedom. Try to see dating as a way to connect with new people and as a path toward finding your youthful, fun side again.

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