Life after divorce dating can challenge your confidence.

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.


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 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

old fashioned picture of man and woman on a zip line

Dating After Divorce in 10 Steps

Dating after divorce is just one aspect of your plan going forward.

Good, you understand that. You know that as a newly independent woman there are many things you need to address right now, and that maybe, just maybe dating shouldn’t be your first priority … But, another part of you is thinking,“Yeah, uh, huh, BUT! WHAT ABOUT dating? When will I be ready? Why isn’t it happening already?”

Well, for those of you (for us) who cannot wait, here’s a list, Dating After Divorce in 10 Steps, because, we are heavy into the steps metaphor, and we know you are curious. We know a part of you needs to know IF you can do this. Can you trust again? 

What must I do to get out there?

1. Create your mission

What is your intention? What are you looking for? Maybe you are saying, you are looking to …

  • Dip my toe in the fishing pool (why is everyone a tadpole?)
  • Find a companion to do things with
  • Not set the bar too high, really, but just go out to dinner with an adult who can use a fork and knife
  • I’d like to spend the night with someone (let’s not beat around the bush)
  • I just need to fill the empty. I am scared to be alone (that’s ok, just pause and give yourself time to be alone with it)

Note: “I’m Looking for My Soul Mate (Again)” is not an option.

2. Write your mission down

But wait, what if I don’t know if I am really ready?

No one says you have to. You are free.

Isn’t that one of the most beautiful sentences? Think about it. You are free. You can date if you want. Or not. But, oh, if you want … YOU CAN DO IT!

We are not saying that stepping  into the crazy world of dating is not daunting. It is cra-zee, scary sometimes, confusing, and over-hyped. We know it summons up all kinds of fears. But let’s not stay in that place, reviewing what we know. Let’s live. Let’s move.

3. So, reread what you wrote for Step Number 2

4. Brainstorm a list

Write down potential locales, situations, friends, and dating platforms that can help you meet someone. Online dating is the best way to find someone, based on our experiences. But you can also join a softball team, go to the bar, prowl the bookstore, hang out in a museum, or linger at the produce counter, channelling movies scenes.

5. Research online dating

If you are one who exhausts all resources by researching the very best way to do virtually everything, than have at it …  make a case-study. Evaluate which dating platform you might use. Interview your single friends, and consider this study comparing different dating platforms. It helps you understand a lot in advance of committing (and boy, do we like that idea).

6. Test your hypothesis

Remember, after all your googling, contrasting and comparing the best ways to date, you still have to try it out– which means conducting field work. You can spend hours inside creating your online profile, or better yet, asking your best divorce friend to author a juicier one, but accept that at some point, you must leave your house for anecdotal material.

7. Get your blood circulating

In case you hadn’t noticed, all action starts with effort. So start your action truly by going for a walk, and not to meet him either, but to find sunlight. To get your endorphins going. To connect with nature. Sunlight, exercise, and nature have an incredible impact on our psyche and well-being. They make things begin to look up like sunflowers. You are starting to look up. In fact, you are positively radiating positivity!

8. Prepare your mind

Read the newspaper headlines, watch the news, read a book, so you have something to talk about other than your job, your kids, or your divorce (the worse!). Seems obvious, but those subjects are tedious to everyone but you.

9. Then do it

Say yes to someone who asks you out for drinks. Or a cup of coffee, or a brioche, or God knows what. But something short and simple, see? Let it happen in a public place like a restaurant or bar, so you can enjoy it (if necessary, briefly and make a fast getaway) or leave an opening for the possibility of dinner — if fried mozzarella sticks suddenly sound more appealing than Netflix at home. (He’s got to be quite a guy.)

10. Afterwards, be fair to him/her and to yourself

Did he seem in alignment with your mission? Were you turned on by him? Could he be a friend? Did he make you laugh at least? Thank him, and let him know within 24 hours if you will be seeing him again or not, and then think about all you’ve learned. What is it that you have learned if you had to reduce it to a one-phrase headline?

Ok, I’ll tell you. It’s: Yes, you CAN!


Since 2012, smart women around the world have chosen SAS for Women to partner them through the emotional, financial, and oft times complicated experience of divorce. Whether you navigating divorce or already rebuilding your life after the overwhelming experience, one thing making a significant difference for women is the conscious choice to not reinvent alone. 

Schedule your FREE 15-minute consultation with SAS. Tell us confidentially what’s going on, and we’ll give you black & white feedback, resources and suggestions for your next steps.