How to Date Multiple Guys At The Same Time

By: Simone Paget |


Dating is often a numbers game. The more people you date, the more likely you are to find someone you really click with. I’m not opposed to dating multiple people at the same time as long as you go about it in a way that’s respectful to yourself and the people you’re dating. Here’s how to date multiple guys (or girls!) at the same time without being shady.

DO go on multiple dates with different guys during the week – If you’re still in the casual dating and getting to know each other phase, there’s nothing wrong with hanging out with a couple different people during the week.

DON’T go on multiple dates in the same night –  Ok, I admit there have been times when I’ve gone on a lunch date with Guy A and then met Guy B for a drink later that day. As fun and bad-ass as having multiple dates in the same day can feel, I don’t really recommend it. If you’re really trying to make an effort to get to know each person, it’s more fair to both of you to space out your dates so that you can focus on one person at a time.

DO communicate openly – Be respectful of the people you’re dating. If they ask if you’re currently seeing other people, be honest. You’re not required to give a detailed breakdown of who you’re seeing and the dates you’ve been on so far, but to set appropriate expectations, keeping the lines of communication open is always best. However, bragging about all the guys you’ve been dating or have messaged you recently, is NOT COOL.

DON’T make up lies – If you catch yourself lying to the people you’re dating about where you are or who you’re with, or coming up with elaborate scenarios so you don’t get “caught” you’re doing it wrong.

DO date people who don’t know each other – To keep things as uncomplicated as possible, only date guys who don’t know each other. To avoid awkward run-ins, make sure you diversify your date activities – bringing different guys to the same coffee shop, restaurant or bar that you all frequent on a regular basis, is just a recipe for disaster.

DO have realistic expectations – If you’re dating multiple people, there’s a good chance that he is too. If you discover he’s been going on dates with other women too, remain level headed and reasonable. Unless things have gotten serious between you two you can’t fault him for doing the same thing you’re doing. This is why open communication is so important.

DON’T date people who are friends or related – Unless you’re looking to end up on an episode of Jerry Springer, dating brothers, relatives, best friends or anyone closely connected is just bad news (and totally shady!) Avoid dating more than one guy who works in your office, lives in your neighbourhood, or is part of your circle of friends.

DON’T get intimate with everyone – A good night kiss here and there is fine, however once you start getting naked with multiple people things can get complicated and feelings can get hurt FAST. Out of respect of the people you’re dating and yourself, hold off getting busy with your potential suitors until you’ve figured out which one you like best.

DO politely break things off with the other dudes when things start getting serious with one of them – Why? Because it’s the right thing to do. Plus, if you’ve actually found someone you want a future with your dating mission was a success!