How One Woman Succeeded at Dating after Divorce

Thinking about dating after being married for years can be intimidating, exciting, and frankly, 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 intact.

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 are six top tips I give my clients and friends embarking on the dating journey:

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.

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), and your fab new fundamentals, and just swap out different tops.

Treat yourself to one new thing

It could be 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. A 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.


Most first dates are sitting next to or across from someone, so what your date will see most is your top and jewelry. Either a simple top and some favorite jewelry or an interesting top and minimal accessories are great choices.

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.


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, "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.

Contributing Writer
Alyssa Dineen has been an editor, stylist, and art director in New York for over 20 years. After she divorced at age 41, she began online dating, and rediscovered herself in the process. Through this journey, she found many people out there that could improve their dating profiles and while doing so, their understanding of what they want. Founder of Style My Profile, Alyssa now helps online daters transform their destinies by taking charge of their profiles and their dating experience with her unique approach of “intentional” dating and self-discovery.

An acclaimed stylist and dating expert, Alyssa has appeared in The New York Times, Today Show, Goop, and You can work with her one-on-one, and she also offers workshops and a membership to be part of the Style My Profile Community. You can find out more at