“Pimpin’” — Dating multiple guys


“Save a boyfriend for a rainy day — and another, in case it doesn’t rain.” —Mae West

I’ve found that successful dating requires juggling several men at once. It is like sales, you have to have a number of prospects in the pipeline. I frequently date several men in the same time period until two of us decide to be exclusive or one of us decides to move on. If you only date one at a time, it takes too long to get the next one in the pipeline.

When I was explaining this to my teenaged nieces, they said I was “pimpin’.” Now hold your hat — their definition of a pimp was not the same as mine. It merely means dating around. Let’s be clear here that dating around does not mean sleeping around. You can date multiple people and not sleep with any of them. In fact, I’d recommend you not sleep with any of them until you decide to be exclusive and you both agree that means letting go of all the others you’ve been seeing. It is not wise or safe to be a “player.”

Dating around takes special skills. You have to remember the guy’s name when you’re with him, unlike the time I was halfway through dinner and couldn’t think of my date’s name (it was a first date). I have been told by a guy pal that when a man can’t remember your name on a date, he calls you “sweetie.” You think it’s endearing; he gets off the hook.

You also have to remember other details that he’s shared, otherwise you’ll ask the same things over again and he’ll think you didn’t pay any attention at all. I’ll share an easy way to track this in another posting.

You have to have the discipline to not talk about your other guys while on a date. This is déclassé. While you can imply that you are seeing others, don’t throw it in his face. He may think you are slutty.

But dating around gives you an opportunity to have multiple activity needs met. One likes foreign films, another opera. One likes to hike, another is a tennis buff.

BTW, he may be dating around, too. Clarify this on the first few dates just to be sure you’re on the same page. When I do this, I always ask if he’s sleeping with anyone. Multiple sex partners increase the risk of STDs. I recommend not sleeping with anyone til you’ve decided to be exclusive, then you both get tested for STDs before going further.

So dating around has its pros and cons. I find the pros outweigh the cons, and open, honest communication is best if you are going to date others simultaneously.


4 responses to ““Pimpin’” — Dating multiple guys”

  1. Paulette Avatar

    Thanks for the amazingly simple yet important reminder that it’s perfectly fine to date different people for different fun reasons. That is one of the best parts of being single (again), that we can choose a different person to share a different activity, rather than expecting the impossible of one person to satisfy it all.

  2. Dating Goddess Avatar

    Exactly! Even after you decide two of you aren’t dating material, you may still choose to be activity partners. You are expanding your sphere of companions. How fun!

  3. Mitsy Avatar

    I am still corresponding with the “cop guy” from Iowa who has not been out of his long-term relationship very long. We play phone tag a lot but did talk some over the x-mas holiday. He will be “on call” for New Year’s eve, so that nixes any New Year’s plans with him. I continue to be cautious with him even though I’m more certain that things between him and the ex are really over. I’m trying real hard to not put all my eggs in one basket.

    In the meantime, I have corresponded and met another guy who is a couple years older than me. He’s a mechanic and lives less than an hour away. He lives closer than cop guy which would be a plus. He came in to the store where I work part-time before x-mas and I was a bit taken aback that he was heavier than his photo looked and has a gut (below the belt) that protrudes like he’s about to give birth. I have dated heavier guys and cop guy is also a bit heavy, but this guy is not porportioned very well. Physically, he was somewhat a turnoff for me. Anyway, I have continued to talk to him since I don’t want to be so shallow about his looks.

    He winds up coming to the store again just to see me last night. I know he did not have to drive 40-50 miles to shop at W-Mart. He has sent me some very “flowery” e-mails claiming that he thinks about me all the time, loves my deep blue eyes, etc. He asked to call me after I got home from work last night and I said he could. We talked a long time, mostly about cars as I’m somewhat of a car buff and he’s a mechanic. This morning I get an e-mail wanting to know if I want to go out and also puts that he’s a bit “crazy” about me and “hopes that’s OK”. Well, upon adding all of the elements together, it ISN’T OK. I’m not comfortable around this guy in person. He is fine to talk to and he might be fine to go out with, but he is clearly wanting more than I am willing to give him. So, I write him back and tell him that I can only offer him friendship at this point. I remind him that I am continuing to be cautious about dating in general (and I have good reason with my past experiences) but that I thought it was only fair to tell him that I would go out as friends and did not know that there could be anything more.

    I have friends who told me to date both of these guys if given the chance. While cop guy doesn’t seem to be exerting as much effort as I’d like, we are still talking and that is still giving him some time to get more fully “over” the ex. Mechanic guy has divulged too much too soon to me. It is fine to think about someone a lot, think they have pretty blue eyes and that you might get a bit crazy over them, but you don’t tell someone that until you know they are pretty interested back…certainly NOT after only a week of meeting the person. I think mechanic guy’s overkill with his words and his 2nd unexpected visit to my job have made me realize I don’t want to get involved. He is too eager, appears too needy, and I doubt that I’d suddenly find physical attraction later that doesn’t seem to be there now.

    So, I don’t do well with “playing the field”. I just wish there were more options for dating. I feel like I’m in a snag with the online dating bit. Will wait until after the first of the year and see what happens. In the meantime, I just wanted to share the latest on my dating woes. :0

  4. Miss Nadia Avatar
    Miss Nadia

    Very nicely written. I’m in my early 20s right now and I’ve been “dating around” for about a year and a half. I’ve made SOOO many mistakes during this time. The worst of which is sleeping with one while continuing to date others. I

    The guy I was sleeping with belted out an overwhelming wave of possessiveness, paranoia, hurt, and mistrust. It was like 20 questions every time I was with him. And since he knew I was seeing other guys I felt like I couldn’t be real without answering truthfully. This situation bled into another, with someone who pretty much refused to believe that even though I was seeing other ppl, he might not be “the one.”

    Painful, yes. Did I learn something? Of course. And its nice to read it here as well. From now on I’ll be sure to keep the “sleeping with” and dating around separate until I decide to make a committment. And I’ve always held true to honesty is the best policy, but clarification is probably a close second. So I’ll be more careful about making sure that me and the guys I see are on the same page.

    Thanks for writing!