If you have been separated and then divorced, especially at midlife after a long marriage, just thinking about a first date after divorce can make you break out in hives and your heart start pounding in your chest. Not only are we nervous about a first date after divorce, but so much happens to our self esteem during divorce that we have to totally re-think whether we have the guts to take a stab at post divorce dating at all!

With the breakup of our marriage, we have probably been wounded deeply enough that we wondered if we would survive. The thought of being vulnerable and hurt again makes many of us say at the beginning of our after-divorce-life that we are NEVER going to get that deeply involved with another man again. EVER!

But then divorce loneliness starts spreading out those devastating tentacles of emptiness and we think, “I want someone, anyone, to hold me close again.” One woman in my first support group said, “I want to put a sack over my head and a sack over a guy’s head and just have a good screw!” She wanted no connections. No vulnerability. Only that human touch and physical sharing that would take her away from her loneliness for a few hours. I’m sure we can all identify.

One of the things you need to decide before you even go onto a dating site is “What am I really looking for? I think most women after divorce who are willing to date are looking ultimately for a long-term relationship. But both you and your date need to be on the same page for the relationship to continue.

  • What are you each looking for?
  • A platonic friendship with no strings attached. 
  • A friend with benefits…. (a lover) with little or no commitment. 
  • A potential long term fully committed relationship.
5-Day Divorce Recovery Crash Course. Take the first steps in your recovery and start healing today! Send me the free emails
5-Day Divorce Recovery Crash Course. Take the first steps in your recovery and start healing today! Send me the free emails

Wait Until Separation/Divorce Is Final

There are many reasons to wait until your separation and/or divorce is final to think about a first date. Make sure you get clarity on the rules of dating during separation and during the divorce process. Your attorney or the court where your separation or divorce papers are filed can inform you about the rules in your state or county.

Some states have rules about separated or divorcing people living under the same roof with someone of the opposite sex for a certain number of consecutive days. It can make a difference in your financial settlement. Remember: You are still married when you are separated and when you are in the divorce process. You are formally divorced when you have the divorce decree in hand. Don’t date until then.

Are You Ready To Date?

You are usually not ready to date until you have done the grief and healing work you need to do after divorce. That usually takes longer than you want it to. But that time especially after a long marriage is better spent figuring yourself out and where you want to go from here … not hooking up with someone just to blunt the loneliness. We may think dating again after divorce will help us heal, but we need to grieve and heal before we date.

Below is how one RADiCAL woman wisely advised in our MDRcommunity:

I do not advise dating very soon. You must first heal or you will be bringing a broken spirit to the relationship. Once you can be happy with yourself you will have much more to share in a relationship. … You must learn to be content with yourself and what will cause you to find happiness. Heal before you date. In this day and age, there are so many narcissistic people out there that you must kiss a lot of frogs to find a prince!!!! Me—I don’t like kissing frogs………. that I know for sure!!!! LOL BriarRoses5

Most people want to start dating before they are ready. It’s often that dreadful loneliness and wanting to feel worthy and appealing that drives the desire to connect. In our MasterPlan program we help you do the ”logistical” work of divorcing. We help you deal with all of the physical, emotional, spiritual separation that has to happen particularly after a long marriage. 

It’s also easier on our children if we wait to introduce a new person into the after-divorce equation. It takes our kids time to adjust to the divorce and even longer to be ready to accept a new person into the family. Having a string of suitors coming and going in your life after divorce is not helpful.

Find A Date

What our MasterPlan program suggests is that you first do the work of figuring out what your own talents and dreams and goals are before you look for a first date since divorce was final.

The best way to find a date is to start figuring out the kind of person you want. Ask yourself:

What are my:

  • “Must Haves” – (Believes in God, honest, has a job, likes to fish, takes care of his body, intelligent, enjoys simple pleasures, etc.)
  • “Deal Breakers” – (Smokes, drinks too much, is not nice to servers, is controlling, etc.)
  • “Nice to Haves” – (Hair, a boat, likes to bike, likes to dance, is a certain political party, etc.)

Online dating services are not for everyone, but I met my now husband on one of the general dating sites almost 20 years ago, and we have been married for 17 years! At the time, I think there were only a couple of sites. Match.com and E-Harmony.com. I liked that one because I could choose the age range I was looking for, how far away he was located, whether he still had children at home? 0The site provided a list of questions to answer that helped clarify what I was really looking for.

One of the questions was: “If you could meet someone anywhere in the world, where would it be?” I said “Fly fishing in Wyoming.” Generations of our family have been going there to fish, camp and enjoy nature for more than 50 years, and I thought, “I’m not interested in anyone who wouldn’t enjoy fishing in Wyoming!” And, it was amazing that my now husband responded and has a strong belief in God and loves to fish! In fact, he has his own boat! (miracles happen!)

I’m living proof that dating sites can work … Even though there are dating sites for every kind of relationship you can imagine, the sites with a track record who have been in the business for a long time are probably the most reliable and dependable for actually connecting you with other people who might be a good fit. 

Basic First Date Decisions to make:

Where To Go?

Once you have corresponded with your potential date and think that maybe there could be a future of some kind, you can decide to meet in person. Usually it’s best to keep it casual. A fancy dinner is often not a good choice. (Too much pressure!) Meet at an art fair, or a pumpkin patch in the fall or a botanical garden in the spring. Museums are a good choice and fun things like bowling. Active dates seem to be easier.

What To Wear On A First Date After Divorce

Not long ago, the Wall Street Journal did an article on how men should dress for first dates after the pandemic. In the article, Ms. Shaklee, a certified matchmaker, “ finds casual dressing refreshing and more comfortable for a more subdued, face-to-face getting to know you type introduction.” That’s true for women, too. 

Everyone is more casual these days. Both men and women just re-entering the dating world should dress in something comfortable and pulled-together at the same time. For almost any public place, tailored, well-fitting pants, or skirts with tights and boots can all be okay. Wear what makes you comfortable and confident! This is a good time to update your wardrobe, your glasses, your haircut and just take a fresh look at your own personal style. But don’t get too crazy especially for a first date!

What To Do

Whatever you decide to do or wherever you choose to go, on a first date (and as many dates as it takes you to feel totally comfortable in the car by yourself with him!) always drive yourself. Let someone know when you are leaving on the date and when you are expecting to return and then be sure and check in when the date is over. Driving yourself has several advantages … safety, control and a sense of independence. 

Below is a list of fun first dates that could get your imagination going. Having an out-of-the-ordinary first date sets the stage for more surprises and removes the stiffness of just going to dinner or to a movie.


First Date After Divorce Tips:

Go Slow & Keep It Light

The purpose of dating is to get to know each other better. Take a deep breath and think of your date as just another person who may be fun to get to know better. Many women feel desperate to “find someone,” especially if their ex left for another woman. We want to feel attractive, desirable and worthy. You already are those things, so relax and enjoy the experience!

Set Appropriate Expectations

Instead of thinking, ”I really want this to work out!” feel confident in who you are and what you want in life and what kind of people you want travelling with you! As Keith Miller and Andrea0 Miller say in their helpful 1981 book, The Single Experience, “We have been brainwashed with the idea that marriage is the only good life and that the primary goal of a single person is to find the right mate. That puts incredible pressure on us! With every date or friendship, we start thinking ‘Is this the one?’…and we push hard to make that one the one!” That mindset makes it hard to calmly get to know each other and simply let the relationship go where it will. 

Pay Compliments

The person you are on the date with may be just as nervous as you are. Take the pressure off of you and focus on helping him feel comfortable. Compliments aren’t just for men to hand out. We as women can find something unique to compliment about our date as well. Something simple like, “I’m impressed you know so much about fishing! “ (Or whatever you’re talking about.)

Be authentic! If you’re talking about some new restaurant, artist or Netflix series you have discovered, don’t be afraid to express your real feelings. And if he asks what you want or like, tell him! Do NOT say, “Oh whatever you want is okay.” Find your confident voice. 

Focus On A 50/50 Talk/Listen Ratio

Some of us on first dates think we have to talk incessantly. We don’t! In fact, let him carry his share of the conversation. There may be some quiet moments, but don’t make too much of them and let the conversation flow naturally. Be a good listener. A big percentage of a good relationship is being “present.” Don’t be glancing at your watch or looking around the room. Focus on him. Eye contact is very important! Smiling is good, too!

What Not To Do

On any date with anyone, but especially on a first date, there are things that you should not do. These actions can sabotage your hopes of really learning about the other person. Learn to listen between the lines to what he is saying. 

Don’t Answer Your Phone

Maybe both of you on your first date could discuss putting your phones away. Turn them off! Get rid of the temptation! It’s okay to be out of touch for a few hours. He will appreciate it.

Don’t Talk About Exes Or Other Dates

Being well on your way to healing from your own divorce is mandatory before you even start to date. Nothing is a bigger turnoff than you bringing up your recent divorce or other failed past relationships. Your date is NOT your ex! All men are NOT like your ex! Your date wants the person he is with (YOU) to like men…to be comfortable with men…and to be willing to let him prove himself. Keep your ex out of the conversation! Even if your date tries to get you to go there, politely say you’re not interested.

Don’t Interrogate Them

If we’re feeling desperate to hurry up and find someone, we often try to find out too much too soon. On this first date, just enjoy each other and the time together. Stay in the moment. You may have already explored some of the safe questions like, “Are you part of a big family?” or “Have you always lived here?” or ‘What’s your favorite thing to cook?” Don’t ask a barrage of questions that seem too personal, and maybe like you’re really trying to figure out if he’s marriage material or not.

Don’t Go Home With Them

One cardinal rule of first dates is that you should never go home or to his apartment with him or bring him to your home or apartment after a first date … or until you are certain that he is worth having a relationship with and is safe and has respectable intentions. There are guys out there (and women as well) who are dating only for the sex. That’s their choice. But it doesn’t have to be yours.

Having sex with someone you don’t really know can be physically and emotionally dangerous, and deadly, too. Jumping into a sexual relationship too soon makes you look desperate and changes everything. It tends to diminish the chance of a deep, loving and personal relationship which takes time to cultivate. You’re worth the wait!

Again, even if you drive yourself home, make sure you have someone to check in with to let them know that you are home safe, and that no one has followed you home.


I read somewhere that people like to be with other people who are excited about life. I think that’s true! We want to be around people who are enjoying life and creating fun, good, adventurous life experiences for themselves.

As I tell my RADiCAL women all the time, “self-confidence is the most appealing characteristic for both men and women.” Remember that fact on your first date after divorce. This date isn’t going to determine the success or failure of the rest of your life. Relax and take the time to get to know another struggling human being better. Who knows what can happen!

(For more tips about healing and moving on after divorce, check out our MasterPlan Program and Community.)

5-Day Divorce Recovery Crash Course. Take the first steps in your recovery and start healing today! Send me the free emails
5-Day Divorce Recovery Crash Course. Take the first steps in your recovery and start healing today! Send me the free emails