7 Things Nobody Tells You About Playing The Field (But You Need To Know)

You don't have to choose just one guy.

Things Nobody Tells You About Playing The Field (But You NEED To Know) getty

Some women meet lots of men online and have a chance to play the field. This makes looking for love exciting, as you get to pick and choose from a variety of guys to find the right one. Yet, this can come with its own set of problems if you don’t know how to handle the social opportunity online dating can bring.

My coaching client, Ellie, had a parade of men who responded to her online profile. Some weeks she’d have coffee or a drink with as many as five new guys. She managed to fit all these meetings into her calendar, but you can imagine how the amount of attention was overwhelming at times.


Ellie was doing something right because she also had a lot of second and third date requests. But juggling her suitors became a concern. So she called me for my expert dating advice on how to deal with the flood of romantic options.

I’m a huge fan of playing the field when you begin dating. There are seven vital reasons why this is a sound strategy for finding love. Here are 7 rules to follow, and the one big mistake to avoid.

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1. Meet more guys than you think you need to. 

There’s no second date guarantee in dating. Regardless of how much fun you both had the first time you meet, you never know who will ask for a second date.

Women are constantly surprised and devastated by this frustrating fact. Rather than waiting around for a man to call and ask, it’s best to see all the prospects who appeal and fit your criteria (as much as you can tell before the first meeting).

That’s why it’s good to "hedge your bets,” because you need to meet lots of men to find a good match.

2. Be willing to learn something from every single date. 

When you date multiple men, there are serious benefits.

  • You learn how to start conversations and keep them going.
  • You boost your confidence as you gain experience.
  • You learn how to interact with men the way that works best for you and them.
  • You figure out how to leave a date early when things aren’t working.

Think of how much more savvy you’d be if you had 20 dates in a short period versus spreading them out over months.

That’s what I discovered when I was dating after 40. Sometimes I juggled three or four guys because they appealed to me and asked me out. Most were one-date wonders so it never became a problem.

3. Flirt, flirt, and flirt some more.

In business, when you’re on a roll landing new clients, it tends to attract even more clients. The same thing can be said for dating multiple men.

One client of mine who used this strategy successfully created her desired deal flow by being friendly and flirty at airline clubs and charity events. She had an absolute blast meeting amazing men before she chose the one she wanted to get serious with.


4. Avoid settling too soon.

Some clients insist they’ll only date one person at a time, see how things go and move on if things don’t work out. This sounds logical, but here’s the rub: you can easily get prematurely attached to the wrong guy, because you don’t know about your options.

The last thing you want to do is shut down the flow of interested men  That’s like telling the Universe, “I don’t need these choices.” I advise not limiting your options so fast. If a man you find interesting wants to meet, even though you’ve had two dates with another, say yes and go!

RELATED: 3 Types Of Guys Women Shouldn't Waste Time On

5. Remain objective.

When you date only one guy, he’ll be your focal point, because there aren’t others to soak up all that attention. Dating more than one guy at a time keeps you from fixating and allows you to remain objective.


The point of dating is to get to know people, so you can choose your best match based on something more objective than just the fact that you've grown attached to him. Playing the field does just that.

6. Follow the "three-date rule."

I recommend my clients go on three dates with any man who is in the “ball park” of what they want. If you go on a first date with a guy and you’re not sure about him — that’s a good reason to see him again.

Sometimes a man can be nervous and not at his best on the first couple of dates, then shines on date three when given the chance. That was true with my husband. Date one was fun, unlike date two which was a dud.

I could have easily kicked him to the curb but decided to give him another shot. Date three was magical! I found out months later he wasn’t feeling well, felt too shy to say anything and didn’t want to cancel. I would have missed out if I didn’t follow the three-date rule.


It takes time to get to know people and discover who could be a good match. Give men a chance by going on a few dates with each one before you start cutting them loose.

7. Prioritize your dates.

I helped my client Ellie create a plan to handle her bounty of men by creating create a plan to handle her bounty of men by prioritizing dates that were most likely to lead to a lasting relationship, which was her goal.

The first priority went to second and third dates, so she could continue getting to know men she’d already met. That helped her weed out guys who weren’t a good match. Naturally, some disappeared as well.


Just remember, if you’re too hard to schedule, he might move on. You need to be available with time in your calendar for dates. If you put a man off for a week or two, he’s likely to move on.

A man’s interest in you has a shelf life like food from the grocery store. There are plenty of other women, so if you’re difficult to schedule, he has other interesting women to choose from.

If Ellie had too many second and third dates in a week, she held off meeting additional new men. Once space opened up, then she’d say yes to first dates again.


Prioritizing simplified dating for Ellie, and she’s still happily meeting men before narrowing her options and choosing the right man for her. Now that you are aware of all the benefits to playing the field, give it a try.

RELATED: 4 Reasons Smart Women Date More Than One Guy At A Time

For over seventeen years, Ronnie Ann Ryan has been a love and dating coach for women. She’s helped thousands of successful single women with hot careers (but a chilly love life) find lasting love. Listen to her free audio program 5 Surefire Ways to Attract a Quality Man.