You’re freshly divorced. Life is beautiful. You’re older, wiser and know more than you did the last time you were single. All of these qualities are working to your advantage. And while my Grandmother, may she rest in peace, was fond of saying, “We all have our own cross to bear”, yours happens to be that your proverbial cup runneth over, and you are dating multiple women.

Blessing? It sure can be.

Cross to bear? If you don’t handle it well, it may be.

I’ll explain why. 

Enjoying the company of  multiple women can absolutely be a blessing. Life is not a prison sentence and neither is dating. You are welcome to date women concurrently, not consecutively. Should one or two taper off and fall by the wayside, it’s par for the course. Not every seed that is planted will bloom. So that spark never turns to a flame, no worries! Everything will be fine, no need to go back to the drawing board and start from scratch. Why? Because you are seeing multiple women. When one interest tapers off, you simply have more time for another woman whose company you do enjoy.

Dating Multiple Women Has Multiple Benefits 

Dating more than on women at a time prevents you from experiencing the potential boredom, frustration, desperation and potential exasperation of being suddenly single again.

As if that wasn’t a strong enough argument for the benefits of dating multiple partners, bear in mind doing so also takes the pressure off of you, psychologically. By dating more than one women, one avoids a scarcity mindset. And while women may feel like oxygen at times, John C. Maxwell explains beautifully how a mindset of scarcity would hurt your otherwise decent chances of success. When living from a place of abundance, a thousand signals go out, spoken and not, that you are comfortable and confident because you know you are wanted and desired by more than one woman, at the same time. Could it be the absence of panic or the presence of confidence that makes the difference, you may ask.  To which I would respond, does it matter?

Primitive? Perhaps. Real? Absolutely

So if dating multiple women has so many positive side effects, why not continue the scenario indefinitely? Great question. Some men do. Serial daters abound. As with all things that boast great benefits, it is important to read the fine print. Avail yourself to certain potential side effects. Which is why the following list of four tips exists. Use as directed.

Tip One: Be Honest

Tip one for dating multiple women is the common sense rule. It’s the “rinse after washing” step on the bottle of your shampoo. You wouldn’t think it necessary. And while you would never intentionally step into your day with a head o’ suds, honesty is an oft-overlooked, yet commonsense top-heavy tip in the world of dating .

Be Honest, With Her

While it’s not necessary to tell her on the first date that you’re seeing three other women, telling her sooner rather than later is absolutely the gentleman’s move for a number of reasons. Firstly, it’s always best that she learn this information from you rather than another source. Always. No exceptions. Not only is it a matter of trust, it is a matter of integrity. Which is to say if you value her trust and are a man of integrity, you’ll be honest with her. From the outset.

By being honest when dating more than one women, you are letting her make the choice as to whether or not she wants to participate at the level you’ve chosen. She may, she may not. But lying to her to keep her in the dark could backfire in a number of ways. Particularly unpleasant ways, especially if you live in a smaller town with a limited dating pool. Women talk and news travels fast. Keep yourself out of the headlines.

If you’re feeling skittish about having an open and honest chat, remember this, we’re all adults. If you’re dating several women, it’s okay to say so out loud. Other adults are used to it.

Be Honest, With Yourself

When dating multiple women being honest with yourself is of particular importance, both in how you interact with these women, as well as how you interact with yourself. For example, if you avoid telling the multiple women you are dating that you are dating other women… ask yourself why. What are you afraid of? That they might all leave you? That you might not have your proverbial cake and eat it too? Or is there another reason, perhaps with more of an undercurrent, in that you enjoy getting away with it. Feeling as though you have the upper hand gives you an edge, and therefore a thrill. Or are you seeing multiple women because you’re afraid to get close to one again? If dating several women is your way of avoiding depth, it may be time to make some adjustments. As an adult, do you want to spend a lifetime swimming in the shallow end?  Be honest with yourself. Identify your motives, and then decide whether or not you’re okay with them.

Tip Two: Be Safe

Dating multiple women means you may be having sex with multiple women. Set aside bravado and ego, and take the necessary steps to protect everyone involved. In case this suggestion leaves you feeling dismissive, I would like to gently remind you to consider the sexual prowess of the women you’re dating. You are seeing more than one woman, she may be seeing more than one man.

Whether or not you’re past the stage of life where pregnancy is a concern, you’ll never be past the stage of life where disease is. For more information and statistics that will motivate action, check out the Center for Disease Control for the latest facts on Sexually Transmitted Diseases. Don’t cut your, or someone else’s, life short because of pride or convenience or laziness or any combination therein. If you’re having sex with multiple women, safety is the only way.

Tip Three: Be Original 

When dating multiple women, do your best to have an authentic, original relationship with each. Recycling is great when it comes to saving the planet, it’s not great when dating. Which is to say, mean what you say and say what you mean. With each woman. Don’t copy and paste the same thing you told one into a text message to another. If you send a picture to one, avoid sending the same picture to all in the name of economy.  This includes songs that get you in the mood, movie quotes that make you laugh, and the shirtless bathroom selfie.  Do your best to stay present in each situation. If you’re treating your love life like running an assembly line, you’re doing it wrong. Scale back or risk the entire line shutting down.

Tip Four: Consider Your End Game

When dating multiple women, your hands and your calendar may be full. Time may slip away from you. Weeks turn into months. Months to years. If you are new to the dating scene, let alone juggling multiple women, consider your end game. If you’re unclear about what you want, no worries.

End game consideration can be as simple as giving thought to what you’re aiming to avoid. Sometimes we are better at defining what we don’t want than what we do. Positive or negative, have a goal in mind. Even if it’s to meet as many women as you possibly can in two years, and then look for a permanent partner again. It can be whatever you want, just give it some consideration. Rudderless ships go where the wind and waves take them. Be your own captain, whatever that means to you.

Take A Raincheck on Desperation 

Dating multiple women can be an enriching experience with multiple upsides. So, have fun.

Avoid potential boredom, sidestep frustration, and take a raincheck on desperation. By keeping in mind these four simple tips, you’ll avoid the stress of looking over your shoulder, being “found out” or causing irreparable damage to your, and her, mental and physical health. All the while, avoiding the potential exasperation of being suddenly single again. Life is beautiful, start living it up.

Help out the next guy.

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