Life After Divorce: 6 Dating Tips on How to Show Up

You might be thinking about dating now that you’ve arrived here in this land of the unknown, your life after divorce; and this particular aspect of it can be intimidating, exciting, and frankly, straight-up terrifying. When my marriage ended I was, or so I thought, eager to start dating, and I set up an online dating profile almost immediately. After matching with someone, we texted for a full week before I was able to go out on an actual date. I felt relatively comfortable the few times we chatted on the phone. He was also newly divorced but had been dating for a few months. However, when the day came of our first date (and my FIRST date in almost 17 years) I was anxiety-ridden! I paced around my apartment fretting about why I shouldn’t be doing this:

“What if I have nothing to talk about?” (which, by the way, has happened NEVER in my life)

“What if I do something embarrassing like trip on my way to the table?” (That might have happened before.)

“What if he tries to KISS ME??!!” (Hmm, scary? Or is that I don’t trust myself?)

I even texted my date to tell him I would probably not be able to make it. Luckily he saw right through my hesitation and eased my worries (– there are compassionate people out there!). I then called a friend who helped talk me off the ledge, and after hanging up the phone, I stared down my reflection in the mirror. I had to rip off the metaphorical band-aid, get my act together and get out the door. I put on some of my favorite music: I needed some serious GIRL POWER music and so I opted for some Rihanna and Beyonce (whom I enjoy now thanks to my two daughters). I put on my new IRO jeans (my best friend convinced me I needed some sexy jeans for my new dating life— the best $200 I ever spent!!) and 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 tease me that it’s become my hobby (I have to say they aren’t entirely wrong!). Over the course of the past few years as I’ve advanced through my own divorce recovery and gotten to know myself even more,  I’ve honed my craft and have actually begun to truly enjoy dating, to thrill in it even. Dating is a skill that can absolutely be learned, and like a chess game, once you have a few good strategies in place you can begin to feel confident enough to take a few risks. The same can be said about how you choose to dress yourself for dating. Once you have your good reliable, strategies in place you can begin to finesse the details.

Based on my now ample experience, here are the suggestions I most often share with clients and friends who need a little boost as they head out the door to begin their dating journey.

Here are Alyssa’s 6 tips for showing up in your new life after divorce:

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! I know I was. 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 new well-fitting, but sexy,bra 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 thereafter in your new and empowered, life after divorce) 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

Remember that most first dates are sitting next to or across from someone. Mostly what your date is seeing is your top and jewelry. A simple top and some favorite jewelry or an interesting top and minimal accessories.

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 romantic 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 don’t go too far on the comfort level. Leave the “sensible” shoes at the office.

6. HAVE FUN

This is not a styling tip but just a “life after divorce” tip. Seriously, this should be a fun experience! This time around, you’re not 20 something full of insecurities. You’re not (necessarily) looking for a life partner. You can use this opportunity to learn more about yourself and whom 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, who after working with me said, “I would walk down the street and feel invisible before, and now I feel a new vitality that was dormant for so long. I forgot what it felt like.” I definitely relate to that and know many other women who have experienced similar revelations in their life after divorce. My advice is to not overthink it and just enjoy your newfound freedom. Try to see dating as a way to connect with new people and finding your inner glow and fun side again.

*If you are in the New York Metro area, email me at alyssa@stylemyprofilenyc.com for my favorites.

Alyssa Dineen has been a New York City stylist for close to 20 years. She has worked with all different personalities, body types and budgets and knows how to help you stay relevant and current while still feeling like yourself — the best version of yourself. Get in touch today to find the styling package that suits you best www.stylemyprofilenyc.com.