Dating Around Online

On the Internet, it’s easier than ever to pursue two, three or more people at a time. But are you headed for trouble? Find out here.

By Evan Marc Katz

he first time I dated two women at once, I was in college. We all lived in the same dorm, but the two girls weren’t friends. After a few weeks of feeling like a stud, I realized that a) feeling like a stud was overrated and b) I had much stronger feelings towards one of the girls than the other. I broke up with one of them and for the next five months, I had my first “real” relationship.

The second time I dated two women at once, I was 24 and living in Los Angeles. One of the women was friends with a mutual friend;
The first rule of dating multiple people is you don’t talk about dating multiple people.
the other, I picked up at a bar. I knew they’d never know about each other, but all the phone calls, emails, and dates quickly became too taxing for me. My charade lasted less than a month. I don’t think I dated for the two months after that.

I discovered the joys of online dating shortly thereafter. Things were never the same. The choices were tantalizing; the faces, fresh and new. The ability to contact (and keep at bay) multiple women was never easier. I found myself corresponding with ten women simultaneously, speaking on the phone to five, and going out with three with regularity.

Maybe I went overboard, but I now believe that dating multiple people (in moderation) is not inherently bad. It doesn’t make you a player, nor does it mean you’re a commitment-phobe. It means, in general, that you’re still not positive that your current relationships are going to turn serious. And who can blame a marriage-minded person for keeping his or her options open?

So if you’re anything like me, both excited and daunted by all the options presented by online dating, keep reading. Understanding these five ideas will allow you to both conduct yourself with class and date multiple people successfully—until you decide to focus on one lucky person. Ready? Begin!

1. Don’t ask, don’t tell
The first rule of Fight Club is you don’t talk about Fight Club. The first rule of dating multiple people is you don’t talk about dating multiple people. It’s that simple. By the very nature of online dating, it’s understood that you’re corresponding with and/or seeing other people. That’s OK. We’re all adults here. While we embrace the concept of honesty, sometimes speaking your mind is actually detrimental. This is one of those times. It doesn’t matter if things are casual, if your date seems cool, or even if he or she has made it clear that you’re not the only one. Rise above the temptation, and keep your lip zipped.

2. Make each date feel special
Your primary job on a date — if you want to ensure a second date — is to make the person feel comfortable. People feel comfortable when you are “present”—smiling, asking questions, making eye contact. Problem is, it’s easy, when dating prolifically, to be less than fully engaged in each individual meeting. That’s no excuse. Just because you lined up a date for every night this week doesn’t mean that your date should pay the price. If you find that your attention’s drifting after your third chai latte coffee date of the day, you’re better off canceling and rescheduling than sitting across from a person who can detect your lack of interest.

3. Know that the rules change once you get physical
A date is only different than a friend at the end of the evening. And while a kiss is just a kiss, it does send the unmistakable message that more physical action may be in store. This is a good thing — a
Casual dating is fun, and sometimes that’s just what you need.
very good thing — but when you factor in multiple people, the situation gets a bit confusing. Suddenly, you’re seeing three great people at once, all of them are at the “Are we gonna sleep together or what?” phase, and you can already see how that’s ending badly. It may not always be realistic to date only one person at a time online, but it’s certainly reasonable to winnow things down to one person if sex is on the horizon.

4. Take your date’s relationship goals into account
Casual dating is fun, and sometimes that’s just what you need. But when feelings develop and you and your date aren’t on the same page, look out. You may be just trying to get out there and shake off your previous long-term relationship, but the people you’re dating may be investing in you emotionally—especially if you’ve gone out more than three times. Be attuned to the needs and long-term goals of your dates because, whether you want to or not, you have their hearts in your hands.

5. If your date asks, tell the truth
If the person you’re dating asks you if you’re seeing someone else, you have two choices: Be honest, or lie through your teeth. Stick with the former. It may be ideal for everyone to live by “Don’t ask, don’t tell,” but that’s not the way it works. Tell the truth, and give your date the option of acting according to accurate information, not the useful and charming illusion that you created. By living by the Golden Rule, you set a positive example and create a trust that strengthens your relationship if your partner decides to stick around.

Evan Marc Katz is the founder of online dating consulting service and the author of the new book Why You’re Still Single: Things Your Friends Would Tell You If You Promised Not to Get Mad. Reach him directly at
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