That’s entirely up to you. It really depends on what you’re looking for. Are you looking to develop a serious relationship? If so, skip to paragraph 2. If you are not looking for anything serious, skip to paragraph 4.
If you’re looking for a serious relationship, the most important thing you can do is be available. Being available is not just a physical activity (example: I’m free to make plans on Saturday), it is also emotional. You need to lighten the load of any baggage you may carry, and be ready to start something with a clean slate. As you get to know someone, you want to listen actively and remember the important things they are sharing about themselves. They are giving you a window-view into their beliefs, their situation, and their history. You should be actively engaging with this person and this person alone, until you find a reason not to. If you are not enjoying this person’s company… stop seeing them. Start seeing someone else. It’s very simple that way.
Some people are simply old-fashioned. They want to be chivalrous and do not believe in dating multiple people. They don’t want to string anyone along or waste anyone’s time. They believe it shows respect for themselves and the people they are dating to only date one person at a time. My only caution is you may be missing out on something by holding yourself to such a standard. Even in the old days, woman had dance cards and men would sign up for a dance. Would you call your grandmother a slut because she danced with a dozen men in one night?
If you’re not looking for anything serious, and you just want to have fun and get out with as many people as possible, then dating multiple people is the best way to do so. You’re playing a numbers game. The more people you date the more likely you are to find someone you really enjoy being around. Maybe it’s nothing serious. That’s totally cool. Go have an adventure and make the most of your time together. You can go to a concert with someone on Friday, and rock climbing with someone else on Saturday. See who you like being around the most, and spend more time with that person.
The hardest part about dating multiple people is cultivating a special bond with any one of them. It gets confusing. Maybe you liked the Friday night person better, but maybe the Saturday activity was more fun. Maybe if you had seen Friday night person on Saturday you would’ve connected with them more.
When I used to see different women on different nights, I would struggle to remember (what I considered to be) trivial details, like how many siblings they had, or what town they lived in 10 years ago. I wasn’t being fair to them. I really didn’t care about them. I just wanted to have fun… and that’s cool, as long as there is a mutual understanding that you are both just having fun and seeing what happens.
If what you’re looking for is something real, you should start it on honest footing and give this person a chance based on their own merits, not in comparison to the hottie with the great ass from the prior weekend. If you’re looking for fun, go for it, but keep in mind you’re watering down the entire playing field. Try not to get too dirty.
– John Powers