How Many to Date At Once?


The way the dating game is played nowadays is like an episode of The Bachelor or Bachelorette, with people openly sharing that they are interested in more than one person.

Unlike The Bachelor, most of us don’t have the deep pockets of a hit television show backing us. We don’t have the luxury of putting our lives on hold for months while we focus on nothing but dating. This begs the question, considering real life limitations, how many dating prospects can an average person juggle at one time?

(Pick your analogy here: how many to juggle, how many irons in the fire, how many to keep on the radar, how many plates to spin, etc…)

There are mental health reasons to date multiple people as well, as diversification is an excellent way to reduce risks against heartache.

I previously asserted that a typical single woman should juggle AT LEAST three men at a time. That example assumed that there was a “Mr. No Commit” in the picture. However, in my opinion even women who are fortunate enough to not be plagued with a Mr. No Commit in their lives should keep at least three men in play. There are many reasons to keep multiple men “on the radar” at one time. Some of the moral and practical reasons that come to mind are:

  • As a matter of principle, you should not put your life on hold until the man makes a commitment to you.
  • Ironically, it makes the man of your dreams value you more.
  • You have a head start on recovery if your #1 prospect does not pan out.

I could list a hundred bullet points here actually. But the bottom line is that being in demand is a good thing. It raises your value. Contrarily, if you give someone a monopoly on love, you will get less of what you want at a higher price. [Yes, I know this disgusts you, but the laws of Economics apply to love just like everything else.]

For me, I need to have multiple prospects in play to keep from losing my mind! As much as it pains me to admit, the harsh reality is that I am completely insecure when it comes to women. I crave approval, affection, and attention from women all the time. I’m obsessed. I don’t recall ever craving female attention as much as I do now. It is not just sex–I want attention. I like texting, talking, touching…all that stuff. It is sad really…but it is what it is and being in self denial about it won’t make it any less true.

This is my weekend with the kids. As much as I love them, I am basically bouncing off the walls starving for adult time. It is too cold to get outside. I lost the treadmill in the separation…I am stuck inside with too much time to think and not enough distractions. That is a bad combination for an insecure dude!

There are a few women I would love to flirt with to pass the time. But doing so will only make me come across as clingy and/or desperate. Not cool at all. For weekends like these, it is good for me to have multiple women to juggle. It increases the odds that one is available to keep me entertained via flirty text and so forth. That way she keeps me distracted so I don’t obsess about the one(s) I’m interested in that are out with other dudes right now.

[Unhealthy spiral? Probably. I’ll cross that bridge another day—NOTE: Any woman who says “you need time to heal” in response to my confessional will be showered with sarcastic comments. Well deserved sarcastic comments…]

However, juggling multiple women is a double edged sword. Flirting with too many women at once screams “player”.  Any woman I would be interested in a long term relationship with will be smart enough to spot a player, and will dump me in a millisecond if she feels she is getting played.

To use Economics parlance, the theory of diminishing marginal utility comes into play here big time. Meaning, at some point the extra benefits of having another woman in play are not worth the costs. There is an optimal number of women to keep in play at once. I just have to figure out what that number is for me.

I do believe that answer is “at least three” until exclusive material is found, and feelings are mutual. But are four too many?

Again, I am not talking about sex. I am talking about women that I am communicating with via phone, email etc. that I am interested in taking on further dates, and who seem to be mutually interested.

I want to set a maximum number of women to have “in play”. Once I reach that number, I do not log on to a dating site again until one of those drops off the list. At some point the diminishing marginal utility is too great and one just needs to work with what he has…

Another benefit of giving oneself a quota is that it makes one become self aware of the quality of the prospects. For example, let’s say I am keeping four women “on the radar”, and yet I still feel a strong temptation to flirt with new women on an online dating site. To me, that indicates that those four women aren’t quality prospects if I am that tempted to find new ones. Therefore they should be culled and replaced with higher quality prospects.

Thoughts? I would like some male opinions on this one…

33 thoughts on “How Many to Date At Once?

  1. Wow, marginal utility totally took me back to college. Way to make my brain think! lol.

    Personally, I can’t handle more than two easily. But I do agree with the benefits of having more than one in play – you don’t end up hyperfocusing on just one woman, so you’re less likely to smother her and drive her away.

    Personally, I’d rather just focus on one woman. But if I have multiple prospects at the same time (which doesn’t ever really happen to me), I’d try to keep them all afloat until I see something strong emerge.

    • You just read on your blog that you went on 4 dates in one weekend! So you seem to be doing well! — I struggled hard to find a date this weekend (one that would show up and not flake out.), so you seem to be juggling 4 nicely. It is 4 “on the radar”…

      • Well enough to get 4 dates, not well enough to make any progress with the 4 different women. lol

  2. Give them a little time before totally ruling them out. But I agree, if you feel the need to keep looking and searching – the current crop isn’t for you.
    And from a female perspective – it’s easiest to juggle 3 at a time. I think it goes for either sex. It keeps your sanity because you still have time to yourself and time to spend with friends. However, you should never let an awesome prospect pass by.

    • Well said. Juggling four for too long is hectic. But there are times when one is on the way out and another on the way in that it becomes necessary. It is tiring though! That is yet another reason why we all want to find “the one”. Thanks for the comment!

  3. I agree. For starters there is never any harm in keeping the options open. When I started online dating last year (I am male) I always thought it would be one at a time “that one didn’t work out? ok… who’s next in my bookmark list”. But no, I quickly the importance of keeping up contact with a small handful just in case. After all, no matter how much chemistry you feel with a person, there is still the chance that there is somebody else with whom they feel more chemistry… and that goes for men and women.

    I knew that a couple of the women I dated were also dating other men. And I was totally fine with it… on the contrary, I was glad they were doing it. In my mind if they see other people and still come back to me then it means they feel great potential and if they don’t come back to me, what the hell, clearly there’s not much there anyway.

    If only we were all so pragmatic about dating we wouldn’t cling to the first person who came along, we’d all have a better idea about what we want and maybe we wouldn’t so often end up with people who are unsuitable for us because we can’t bear to be alone.

    • If the world worked the way I wanted it too, I would rather date one at a time in rapid succession. But the modern world is more like an episode of The Bachelor. I hate it. But I’m not going to single handedly change culture. Unlike you, I get jealous when someone I’m interested in is dating someone else. Yet another reason to keep irons in the fire–keep from losing my mind!

      • But saying that, the girl I connected with at the beginning of this year (felt so much chemistry with her and after just two dates it seemed to be heading somewhere) that I lost interest in contacting other women. She unfortunately had unresolved issues with her ex and they got back together. I’m still hoping down the line we might get a shot but I’m not hanging on for her… she knows how to get hold of me and she knows I’m interested because I said “I’m disappointed you got back together because I felt we really had something”.

        That iron is not yet out of the fire, but I’m not hanging around for her.

  4. I don’t agree at all. I think this is a correct course of action if you absolutely need to have a date every weekend. I think it is awfully hard to get to know someone when you are juggling 3 or 4 men. I did the serial dating thing. I bIew it with a couple of nice guys. I am waiting for a nice guy and then I will invest a little time to get to know him. I do not need to worry about my “value.” Mainly because I know I am awesome-my value is set when I walk in the door (yours should be too.) Just because I choose to spend time with only one man doesn’t mean that I am not desired by others. It means that man is worth my time. Dating is only a game when you are dating a player. (On a separate note, this is very well written and I am not saying I don’t see your point.) I’ve just been playing long enough to know I want something real and I don’t need to keep dating a bunch of men at once to find it.

    • I just want to emphasize that I am not talking about anything nefarious here. I had 1st dates with two women this week. Each of whom openly talked about how I was their 4th date recently. I appreciate the fact that they were both open about it. I have higher opinions of them than the women who tried to BS me about the numbers of men they were flirting with. Internet dating has changed the standards. I am meeting these women off the internet. The rules of engagement are set by them, not me.

      Incidentally, I have a 2nd date with one tomorrow. The other pulled “the fade” on me. Win some, lose some. That too is part of the process. The fade didn’t bother me because I had other irons in the fire, or other plates spinning, or balls in the air….(pick your analogy).

      • Oh you may be internet flirting with more than one but I will stand firm that serial dating produces more dates with players than anyone else. I am looking for a quality man and a long term relationship. How can I manage my career, be a good parent and get to know a “good” man-making him feel special and all that jazz- while serial dating? I can tell you my career and parenting skills will never be tossed aside so that leaves me with not being able to pay attention to the man. Also, I know women are playing you. I was getting played BIG time when I was serial dating. That’s becasue dating is only a numbers “game” when you are dating a player. I chose not to play. I’m looking to meet someone real.It was very empowering to make that decision. If a man disappears and tries to come back-he’s playing me and I’m done with him. Now I say all that and I will step off of my soap box and qualify that with: I used to serial date. It was fun for a minute. If that’s where someone is at-more power to them. I am not judging. It is fun in its own way. I just can’t cuddle and share true intimacy with a stranger is all 🙂 BEST of luck to you my friend!

      • I totally get what you are saying datinginvegas but for me, the concern is that if I fall (or invest a lot of time) for somebody too early, and get my hopes up too much, I’m leaving myself open to being gazumped by a better offer… no matter how brilliantly I think things are going. I discuss the perfect example of this happening to me here. The second date with the girl discussed in that post could not have gone any better. We agreed to a third date, she messaged me later that evening “can’t wait to see you again” yet that did not happen. I do not feel she was being deceptive… had she not met her ex I firmly believe we would be in a committed relationship now.

        And what if I’d told any other girl I might have been serial dating “sorry, met somebody and it looks as if it is going somewhere” I’ve closed the door and couldn’t go back. The point is, keep your options open because anything could happen.

        Internet dating levels the playing field a little more for all of us… and I think some women do not like that they no longer hold all of the cards (let me point out that I am not levelling this accusation at you).

      • Chin Up, Sorry to change subjects. But how did you get your link to appear so? Yours looks visually appealing. The one I posted above does not. Does HTML code work for comments?

  5. If you have the option to juggle 3+ women at a time, I say go for it! I rarely have that many prospects at one time but if I did, I think 4 is a pretty solid number. Like you, I want attention…So I totally understand what you’re saying. Great post! 🙂

  6. I am fully in agreement with you smoothreentry, and above blogger! I too have insecurities and the ‘irons in the fire’ keep me feeling attractive and empowered. I don’t need a man for that specifically but it does help. Plus it does mean you get to socialise a lot more!

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