It’s a Date! Getting Ready to Re-Enter the Dating Scene After Divorce

Getting ready to re-enter the dating scene? Check out these “Dos and Dont’s” plus the 5 “rules of engagement” for dating after divorce.

TX FAQs/Prenuptial and Postnuptial Agreements

The general rules for “re-entry dating” are like the general rules in life. They are the unwritten codes of conduct that most of us understand but don’t always follow. (For example, if you feel overweight, don’t talk about how heavy you are around someone who is heavier.)

It won’t be easy at first. Knowing the rules is one thing; applying them is another. But trust me: you can do this! You can! You are a divorce warrior, and it is just a date. So before you talk yourself out of it, here are a few general rules for that uncomfortable first post-divorce date.

Rule #1: Act your age and dress age-appropriately

If you need some help, just comb through a clothing store catalog for some ideas. Go to a department store and see what’s on display. Ask for help. Sales associates love a dating mission. Polish your shoes, and bring breath mints. For men, trim all facial hair and “unibrows”. Pull out the tweezers, for goodness sakes. Ladies, too! Now go and have fun!

Rule #2: The first date should not last longer than two meals

You can pick which meals, but I recommend starting with just coffee. This date is the “Meet and Greet” date. It is short and sweet and, if you hit it off, it could turn into lunch. If the date isn’t going anywhere, you can save your money and get on with your day. It’s just safer that way.

Rule #3: Always have a Plan B

If you learned nothing else from your divorce, you should have learned to always have a Plan B. This is a must! Anyone who has survived a divorce has had to kick Plan B into overdrive at one time or another. Plan B is what paid the mortgage the first month after you were separated. Plan B is what got you through when alcohol was not an option!

When it comes to dating, always have something to do later. Have a friend call and check in to see if you need rescuing in case the date is a dud. This is why I never recommend dinner for the first date. If you are the one paying, it can get costly. Spending money on people you will never see again is a bad investment. Spend your money wisely; keep the first date short and sweet.

Rule #4: Do your research when choosing a location

If you are at all like me, your first “naked” encounter will come way before you take off your clothes. I’m talking about that first blast of humility you get when you walk into a bar for the first time in ages. Suddenly the Emperor has no clothes — and tag, you’re it… you’re the Emperor! A good rule of thumb is this: if you’ve never heard the music playing, then you are probably in the wrong bar. Better places to go are hotel chains that cater to an older crowd for dinner and dancing.

Rule #5: Never bad-mouth your ex

If you just raked your ex over the coals, don’t brag about it. That kind of stuff in no way will impress a potential date. It won’t be funny to them. Chances are, either they themselves were, or someone they know was, treated unfairly in a divorce, and you become an easy target. Avoid talking about your troubles on a first date, period!

Re-entry dating dos and don’ts

By the end of our divorce, we crave companionship, but the reality is we are not ready for another relationship, even if we think we are. We want to date, but the chances of being successful depend on how you define success. If that means having sex, then a meaningful relationship isn’t in your plans. But if successful dating to you means finding your soul mate, then your odds increase when you understand your own shortcomings. Most divorced people learn this after they’ve been doing the dating thing for a while and nothing solidifies. They soon learn that it is important to take time to rediscover themselves first.

Let’s say you’ve spent time rejuvenating yourself and you are now ready to date. Just know this: what you thought worked in your 20s may not work for you now. Besides, how long ago was that, a decade or two? The whole scene is different now. To get you up to speed, here are some lessons and principles that will help you meet and grow with that special someone.

Don’t rush into a new relationship

When a relationship is new, everyone is on his or her best behavior and intentions of being a good partner are 110%. Moreover, when the sex is good, a new couple can’t get enough of each other. Pretty soon they know each other’s schedules and are thrown into an unspoken commitment. Suddenly, when one person needs space and the relationship its halted, the one left behind feels used. These romances beg for air. When no space is built into the relationship, it is safe to say it began with neediness. If this situation is all too familiar, then my next bit of advice may shock you. This wouldn’t happen if everyone would just settle down and get out of heat!

Don’t let your sexual activity exceed your level of commitment

Many people think “not rushing” means waiting a month or two to have sex. Not so. Not rushing things means waiting to get to know the other person before you have sex. That can take much longer. In today’s dating scene, waiting this long would seem abnormal to most people. That’s because our society is so impatient and the expectation is that if you haven’t “gotten any” by the third date, there must be something wrong. Don’t let your sexual activity exceed your level of commitment.

Don’t assume you’re committed

You are not committed to anyone until you have talked about whether it is mutual. If you feel like playing the field for a while, then do that and don’t feel guilty. Make no assumptions when it comes to commitments. This is difficult for the newly divorced because once you have been divorced, you seek comfort in absolutes, and knowing where you stand in your new relationship is one of them. Be careful though, because this can frighten a potential partner who has been single for a long time.

Too often when commitments are implied, a misunderstanding happens and one person gets hurt. So before you speak to your partner about commitment, ask yourself, “What do I want?” Do I want to keep it light with Brian and see what happens with Rich, or jump into another serious relationship? If the goal is to find yourself but have companionship along the way, now is not the right time to commit to anyone but yourself.

Do recognize relationship “end-its”

Not all post-divorce relationships are equal, and the reasons for their ending can seem unclear to us if we are the one dumped. Here are typical scenarios:

  • The rebounder sexship
    Rebound relationships, or “sexships,” are based on sex and companionship. The re-bounder is usually the first person we have a pseudo-relationship with after a major breakup. If they are clued in, the rebounder will know their status and will proceed with caution. So here’s the tip: Being the rebounder is risky and is best left to people who want to fill a temporary void in someone’s life. The rebounder should realize there is no future in this relationship. It is what it is. Trouble is, the rebounder may not see himself or herself in this light. He or she may therefore not entirely understand when you suddenly tell them you might have unresolved feelings for your ex. So how do you avoid becoming the rebounder? Ask your partner this simple question, “What would you do if your ex came back tomorrow?” Their answer will be very telling. (The only answer you want to hear is, “That already happened, and it didn’t work.”)
  • The relationship of convenience sexship
    This relationship is based on one thing: convenient sex. If you were involved in what you thought was a relationship and it ended suddenly, perhaps what you were in wasn’t a relationship at all.

And — finally — do try to relax

Dating after divorce, for the most part, is like learning to scuba-dive; you might just want to start out snorkeling on the surface before you put on the oxygen tank and go for the deep blue water.


Tomi Tuel calls herself a “divorce warrior”. When her marriage collapsed with little warning, she picked herself up and started fighting back. In her book, 101 Things I Learned After My Divorce, she uses humor and honesty to openly share her fears, insecurities, and challenges as she embraces self-discovery and renewal.

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