Post-Divorce Casual Dating: To Fling or Not to Fling?
Two of my three kids are grown, so I think I can safely say now that I wish they had taken a gap year between high school and college, or during college. At least they studied abroad.
The amount of worldly knowledge and independence they gained from studying abroad got me thinking about the corollary to dating after divorce.
Bear with me here. Marriage is for amateurs, looking for the obvious answers. It’s a good place to learn within the confines of a very rigid structure. But it doesn’t teach you everything you need to know about yourself, love and sex, and long-term partnerships. Just like high school, your marriage served a purpose, and hey, no regrets, but you might have missed some key learnings when you were stuck there.
In this analogy, high school is marriage. You're not there anymore. You're divorced. You are free. You've grown up.
Did you take the opportunity to do "a gap year?" Did you even study abroad—or are you:
Wanting to stop studying love and sex altogether
Manically looking for the next structured learning environment (i.e., to settle down with the next likely candidate?)
What if you thought of dating after divorce as backpacking through Europe or going on safari—a chance to see SO many new things before you decide on an ultimate course of study or career path? Doesn’t it seem wise, though scary, to think about it this way?
As a dating coach for women over 50, I notice a trend in the dating world:
At some point, people burn out. They forget they have plenty of time to figure it out and that it can be an awesome adventure, full of learning and growth.
Given this perspective, I recommend something different to those divorced people who are ready to date again but aren’t sure they ever want to settle down or get married again.
I’m calling it the dating “gap year.”
It doesn’t have to be a literal year, but it does need to be a set amount of time—at least 6 months—to really do its job of fostering your courage and exploration.
Casual dating is completely different from looking for a long-term partner. Determining your criteria for dating and making a 3H chart (head, heart, hoo-ha) will still be necessary, but the requirements will be different for casual vs long-term.
For once, you get to weigh hoo-ha over head. However, there are still important head and heart criteria that should be in place if you want casual dating to turn out to be a good idea.
Vetting Potential Partners: Are They Fling or Real Thing Material?
If you’re leaning into casual dating, you don’t need someone who is making promises about forever. What you do need are potential partners who:
Understand and respect your boundaries. You said you just want casual, and they said, "Great!"
Can be upfront about their intentions. From what they share about their pasts, their goals, and their dating life, you're clear they have the same intention.
Don't get upset, threatened, or flustered if you bring up your desire to be casual or that you are seeing other people.
Don’t reveal red flags like jealousy, love-bombing, asking for commitment, or trying to monopolize your time.
The dating pool is full of different people, looking for different things. Some want true love in a long-term committed relationship, some want casual sex with multiple partners, and everything in between. And some people are confused about this, though they might not admit it.
That’s why it’s crucial to ask: Is this new partner a good fit for the dating experience you want right now? Ask them AND ask yourself.
Questions to Ask to Determine If the Person Is Fling Material
Here’s a list of simple questions you can ask on a first date or second date:
“In terms of dating, what are you looking for right now?”
“When was your last serious relationship and how was it for you?”
“How do you feel about casual dating?”
“What’s your comfort zone when it comes to commitment?”
What's your opinion/experience with monogamy? Casual dating?
Notice—these aren’t overtly deep connection questions, and that's on purpose. They’re practical, and they are lining up a casual affair without showing your hand first. They will help you get a better sense of whether you’re about to waste much time with someone who wants something serious.
A wonderful man who’s not ready to settle down may be the perfect person for a dating “gap year.” But if someone is secretly auditioning you for commitment, you’re not aligned.
How Often Do I Need to Re-Message My Lack of Commitment?
The answer: more often than you think.
Many single people hear “casual” and assume it means “until I convince you otherwise.” You may need to remind them a couple of times that you are committed to not being committed right now. That’s the best way to avoid confusion. If they are fresh out of a previous marriage, they may be right on your same page, and on the other hand, they might be craving structure and more of a "sure thing."
You don’t need to make a big deal out of it. Just be clear, calm, and consistent. A simple, “I really like spending time with you. I just want to be honest that I’m not looking for a long-term relationship right now,” works.
Remember: repetition protects you. You don’t owe anyone a committed relationship just because you’ve gone on a couple of dates.
What if He Pushes for Commitment?
It's kind of amazing how much more men generally want a commitment if you are not offering it. They do love a challenge.
But this is where your open heart and open mind get tested. Will you be true to your gap year, or will you submit to pressure, external or internal?
If a man pushes, it doesn’t necessarily mean he’s the wrong person—but it does mean you’ll need to hold your boundaries.
If you feel pressured, that’s a red flag. The right person for a casual dating season will respect your pace. If he can’t? That’s your cue to gracefully end it, not to bend your own needs just to keep him around.
This is the thinking: saying no to one man who’s in a rush clears the path for new people who want the same thing you do.
The Conversation to Establish Non-Monogamy
Ah, the tricky part. If you’re going to have more than one casual partner, you need to be transparent. It's about more than a culture of honesty; it’s about safety, both emotional and physical.
The conversation can sound like: “I’m not looking to be exclusive. I’m dating different people right now, and I want to make sure we’re both safe and respectful about it.”
Yes, it feels awkward the first time. Remember, you’re not asking for their blessing. You’re sharing your reality so they can decide if it works for them.
Once you are on the same page philosophically, you can agree on what the rules will be. Some couples are fine with being open as long as there is only intercourse in the primary relationship. Some are fine with casual sex with multiple partners as long as protection is being used and everyone is getting tested. And of course, others might want to be open-minded but turn out to have hang-ups with non-monogamy as soon as it's in practice. Revisit how each of you is feeling about the arrangement and the rules regularly.
Should I Have Sex in This Context? How Do I Make That as Safe as It Can Be?
Another option while casually dating is to NOT have sex at all, but you might be missing part of the point.
Here’s the thing: casual sex is always your choice. Some women feel empowered by it; others feel depleted. Your job is to know which camp you fall into.
If you do choose sex, the most important thing is safety:
Protection always.
Clear agreements around exclusivity (or lack of it).
Emotional check-ins with yourself: Are you enjoying this, or are you secretly hoping it turns into something else?
Sometimes casual can turn into something more, but it's a bad bet, so if you're secretly hoping for that, it's time to change your agenda and your dating pool.
Is It Still Casual if I’m Only Seeing One Person?
Yes. Casual dating is defined by intention, not headcount.
You can absolutely date one man casually as long as both of you agree it’s not a committed relationship. A single person in your life can still be part of your “gap year” experience.
The best thing you can do for yourself is to keep checking in: Am I still aligned with my dating goals? Am I drifting into wanting more, or is he? Or are we both happy keeping it light?
How Long Should I Stay If I Am Committed to Keeping It Casual?
This is where you’ll need your own internal timer. For some, 6 months is the perfect amount of time. For others, it could be way less. Relationships tend to lose their luster around 7 months, so I'd recommend getting out before that mark. At that point, if you are with your forever person, the relationship takes on different, deeper tones, and the initial flush of excitement is replaced by something deeper, but that's not your goal in the gap year!
The end of your marriage was a major life change. So take the amount of time you need to be free and experience all that dating has to offer. But also give yourself permission to move on when casual dating has taught you what you needed to learn.
What Do I Do If I Want to Transition to Long-Term?
Good news: nothing you did in casual dating prevents you from seeking a healthy new relationship when you’re ready.
Not sure if you're ready to date like you mean it? Take my 5-minute quiz!
If you meet a wonderful man during your fling era and decide you want more, you’ll need to have a clear conversation. The first step is admitting it to yourself. The second step is asking him if he’s interested in the same.
And if the answer is no? That’s not failure. That's actually success. He stayed true to the original intention. Then it's the right time to close that chapter and move on to new possible partners that fit your criteria for long-term love.
This article was meant to give you the how-tos to do a "gap year" well, but if it had the effect of showing you how committed you actually are to long-term committed relationships, groovy! That's great too.
The point is being true to yourself, no matter what society, your parents, or even your friends think is best for you. Especially for women at our age, it's sometimes a little taboo to admit you want something casual. But I am saying, it's more than okay, it can be extremely important: empowering, educational, pleasurable, and fun!
It’s your gap year, your safari, your backpacking adventure. The most important thing is that you use it as a chance to discover your own needs and your own wants before you sign up for another round of long-term love. You know what doesn't work, now it's time to figure out (from experience) what does.
Live a little!
Love,
