Dating is a game of numbers, so date often and date many. Some may find this piece of advice frivolous or wanton, but I think it’s just smart dating practice … and I know I’m not alone.

The rise of Internet and speed dating, which encourage us to connect with many potential dates in a short period, have made dating more than one person at a time much more acceptable. In one evening spent in a singles’ chat room or going through several five-minute mini-dates, it’s possible to fill that social calendar for the next several weeks. And many singles do.

Dating and relationship coach Catherine Wood says dating multiple people, during the pre-commitment stage, can help make us more discerning.


“Oftentimes, people can become serial daters, jumping from one relationship to the next, but if they had spent the time getting to know the person they are with (before getting into a relationship) they might not have chosen that person,” says Wood. “Dating multiple people puts less pressure on you and on each date. As a result you are not too wrapped up in one person too quickly. It allows you to be more objective.”

But being objective isn’t the only thing we can learn. For the truly apt at dating in multiples comes a level of organizational skill. Palm pilots and agendas can quickly become useful tools when dating more than one person, as they help to keep straight the times and places of dates. I even know of some technically savvy daters who have resorted to spreadsheets to keep their dates’ names in order.

Although there is no set rule on how many is too many to be dating, Wood is quick to point out it’s important to treat each date with respect.

“If you realize you are starting to tell someone the same stories over and over again, then perhaps you’re dating too many people,” says Wood.

But no matter how many people are on our dating rosters, this number can, in the initial stages, be kept to ourselves.

“If you are not sleeping with someone, then you are not obligated to tell them you are dating other people,” says Wood. “It’s like applying for a job; you wouldn’t tell the employer you are applying for other jobs as well.”

If the topic does arise, however, Wood suggests being honest. “Simply tell the person that although you are interested in them, you are also interested in others.”

After all, when we do decide to dump the dating spreadsheets and palm pilots for one stable relationship, it’s best to start it off on honest ground.