How To Date Multiple People At Once Like a Pro

I just saw this as a question and it reminded me that I've developed a working system for how I serial date to really unfair levels.

Ok, so I'm going to skip ahead to actually having some people you want to talk to and see/date. How does one keep such a schedule with any consistency?

How To Date Multiple People At Once Like a Pro

1) Start slow with only 2 or 3 and go no further than 10

A lot of people want to have a different person for each day of the week. Slow down. It's hard mentally to make the shift from one person only to multiple people at once...yet it can be done even to the most romantic sap. Also if you go too fast you really start to forget who told you what, people's names, etc...

2) Dedicate an hour

It is extremely easy not to have a life outside of texting your people 24/7. I'll send a few texts to keep the conversation going but ultimately I will probably talk to them 5 to 15 minutes a day during an hour i've blocked off where I can call and see what's up. I tend to avoid "checking in" as this is what a cartoon of someone dating multiple people would do. Instead I simply budget multiple relationships and aim for consistency over actual quantity of time. Some might say an hour a day isn't enough but I really value having a life outside of dating...

3) Don't afraid to get nerdy with your organization game. Use a cheat sheet

When I'm in my prime, I have an excel worksheet with the girls I'm talking to another column for girls I consider girlfriends/friends with benefits, another column for my benchwarmer friends with benefits, and out of towners for when i come through a certain city. This sounds like overkill until you start using it and suddenly everything becomes really easy to track and understand even among multiple girls with only minor updates needed when you meet someone new.

4) Always have someone on back up and privelege people who are closer to where you live

The reason for this is if a date goes badly or somethings just not working out or if you have a flake you can call up the next girl or at least a girl who's your ride or die to let you get some if you feel like you need some TLC that night.

5) Pay in cash

This is hard when paying for drinks or dinner as the bartender or waiter has the bad habit of reading the name on the card sometimes. For women too, avoid doing anything that reveals your last name until you're ready to be exclusive with this person as stalking can easily ensure regardless of gender...

6) Think of dating as an ecosystem. Run people through your system

Ideally, you should be having numbers coming in and coming out. Whether you simply found out they weren't your type or got what you wanted out of meeting them its very often people fall off. in fact, in order to date new people you need some people to fall off which is why you can afford to be a little picky.

7) Use your Calendar and contact photos

You can tell siri to schedule the date so you don't forget. Also always have people send you contact pics so you have a mental note for remembering who they are.

8) Have sex with them before becoming exclusive

Temptation for both men and women is to hold off on sex when you REALLY like a person. nothing could be more erroneous. Sex is THE SINGLE BEST way of bonding with someone to you if done right. I'm not saying rush into sex but don't get lovestoned on someone before you've gotten naked with them or you're just asking for trouble.

How To Date Multiple People At Once Like a Pro


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Most Helpful Girl

  • the requires spending ways too much time with other people. you'll forget how to be on your own. this is like being clingy except deluding it through many people. so maybe they dont feel but but its still clingy and unhealthy. in my opinion.

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    • also hw can you ever mistake one story for another. do yo forget what friends told you what? i dont see how its possible to confuse peoples story unless you are literally paying no attention. I've never mixed up a story with anyone and i talk to many people often. i just can't imagine how that happens..

    • It does though

Most Helpful Guy

  • Excel spreadsheets man. Save my life too. I have a column for details during my conversations so that I remember some tit bits. I do my best to fill them in when I can. So before I go out or to her place I quickly give it a once over 😂 It works. That and google calendar.

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    • Yes google calendar so you know who you're taking out tonight !

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What Girls Said 3

  • Good advises but why would anyone date multiple people at once?

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    • It spreads a wide net. For one you have more sex, but that's more of a fringe benefit. The bigger deal is that you get to know a lot more people which oddly enough allows you to be more picky (as the posted suggested). I mean, if a girl is a little crazy or annoying, you just stop seeing her because your tolerance level has completely dropped. It allows you to be (or at least seem) more spontaneous. Let's say you want to try out that new Cuban place on Saturday and that production of 'Wicked' is in town. You can call your favorite prospect, act like you just came up with the idea and see if she's interested. If she's busy, you just call the next one. The biggest negative is that being a serial dater requires that you be pretty well-funded but if you can fund this behavior, it's no doubt the most fun way to date.

  • How to date multiple people at once: Don't.

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  • pay in cash wow so smart

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What Guys Said 6

  • I think that is a cruel thing to do to someone if you are the only person they are dating at the time and think the same about you.

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    • Nah it's still the getting to know phase then they become friends with benefits if the sex is good they never mind

    • well that is where we disagree. thank you

  • I used to date like crazy when I first graduated college. I would say that that those several years after college were probably the best years of my life! I mean, the travel, the restaurants, the shows, the sex... That said, I agree with all of that except the cash one. I'm not sure what you're worried about exactly there. Cash is so restrictive. I mean, who possibly carries enough cash to date? If you go to a hipster restaurant, your bill is going to be at least $70, often closer to $100. I mean, maybe people do carry that much cash, but I consider cash to be extremely valuable and reserved for only things that require cash (e. g. hole-in-the-wall ethnic eateries).

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    • she can either see your name on the card or sometimes the waiter will read the name on the card and thank you with your full name for some reason

    • Hmm... knowing your (full) name doesn't seem like a big deal to me and as such, it never was to me.

  • Can you imagine the amount of stupid conversations you'd have to endure lol My brain would probably fry by the end of the third date.

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  • Frankly I don't want to date more than one person at once. I will feel lucky just getting one!

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  • What the actual FCK lol

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