One Date, Two Dates, Three Dates, Four!


I’m back, it’s Millie with Millie in the City Matchmaking with the number one dating and relationship forum in the Washington, DC Metropolitan area.  Now that we have gotten that out the way, I want to discuss Multiple Dating.  So in honor of that, this article is appropriately titled: One Date, Two Dates, Three Dates, Four!

I have been talking with Single Women again, as I tend to do, and many of them say that they have been in some series relationships and some have been in some not so series ones.  These women have admitted that these relationships have ended because of their shortcomings, some ended because of the man’s shortcomings, and some ended because they/the man/ or we were so desperate to be in a relationship that we took what we could get, regardless of actual compatibility. With that said, many of the women said that they realized that they might be in a stage in their life where they honestly couldn’t rely on their own judgment when it came to men.

I myself can be held accountable for practically doing the same thing as these women so I, and these women, are trying something new.  Now we are being open to dating in multiples.

Here is what we have learned so far:  (Do’s & Don’ts of Dating Multiple People):


DO – Date multiple people – If you are doing your single thing, go on with your bad self!  There’s absolutely nothing wrong with seeing multiple people at the same time.

DO – This is your chance at an attempt to get to know the men you are dating rather than just sleeping with them.  Now, dating multiples is one thing, having sex with multiple is another thing entirely. Personally, I’ve got love for both sides, but I highly recommend making a sincere attempt at getting to know those you choose go out with. After all, isn’t part of finding yourself figuring out what kind of people you’re really into?

DO – Use condoms, for Goodness sake!! – Wrap it up, THE END!

DO – Be Honest – If you are your dating, please be honest and just say, “I’m dating”.

DO – Clean up your tracks – No one wants to know that they are sharing.  Even if you, your partner, and his mother knows that you are dating and/or sleeping around, it is common courtesy to erase all traces of another man sharing your bed/house/car/whatever with another.


DON’T – Feel guilty – If you are upfront and honest and not secretive about your actions, there is no reason to feel guilty. There’s a big difference between confessing your love for someone and going out to lunch or dinner.

DON’T – Cultivate feelings – Let me be clear, having feelings is not a bad thing, in fact, I am an advocate and encourage it. What I am saying is that if you have already established that you are keeping it casual—-then Keep it casual.  Whatever you do, don’t say you feel nothing when you actually feel everything. This point is one I’m still working on myself, so don’t feel bad if you can’t be cool as a cucumber 24/7.

DON’T – Kiss and tell to someone you’re kissing. – This should be obvious, but sadly, for many it is not. I am pretty confident in assuming that no matter the gender, we as humans don’t like sharing private parts—or at least, knowing that we are sharing.

DON’T – Overbook – Never schedule one meeting on top of another.  The chances of overlap are just far too great, and the consequences are even greater.

DON’T – Assume that you are – This is another obvious one.  If you are dating casually then you mustn’t assume that who you are dating is not doing the same casual dating thing that you are doing.  PSA Announcement – Don’t casually date if you can’t handle it.

In conclusion, there is nothing wrong with casually dating to figure things out so you don’t end up getting hurt or hurting someone else.  After all, this is all about you! You’re not obligated to do anything other than look out for yourself, so go out there and Date and go out on Dates!










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Millie Holmes


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  • Lady K had this to say:

    First, people have to define what dating is for them. Dating could be just going out to enjoy the couple of a variety of people with no intention of getting serious. But for some, it could dating with purpose. I’ve dating multiple men until I felt I narrowed down who could possibly be the one. There are times where dating one on one was more appropriate for me. It just depends on where you are in your life. I know some women who are not comfortable with dating multiple men because they feel you have to sleep with them all. That is not true. You are in control with what level of dating you are in. It’s a personal decision that people just need to be honest about and comfortable with… Now I will go read your article before I get back to work.

  • After reading the article, lady K said this:

    We pretty much said the same things… Dating is just that…going out and getting to know each other. Courting is another level, that means you moved beyond getting to know that person and you are moving in a direction to be serious (one on one). Some women may feel they are in a “courtship” stage, but truly the situation is just dating. Dating = going on dates to me. Intimacy is introduced way too early in many situations, but I need to reserve my comments on that for now!

  • Lady S had this to say:

    I remember watching an old episode of “The Game” when it was on the CW and the character Melanie had decided to do the multiple-partner-dating thing. It seemed like she was having the best of both worlds, but what she discovered was that it wasn’t her scene at all. She was actually cheating herself out of something more meaningful – which is what she ended up desiring.

    I date with a purpose. And I date with monogamy/exclusivity in mind.

    There was a time in my life when it was exciting to see more than one guy at a time, but that’s when I wasn’t looking for anything other than hanging out and having fun.

    Now that I’ve been there, done that and have children – it’s all about stability and loyalty. If I’m into a dude, I don’t want to share him with anyone else. I want his focus and attention to be on how to please me and only me and vice versa.

    I’ve actually had to end relationships because they weren’t “going anywhere” and although we had good times, the dating relationship or “situationship” was draining my psyche.

  • Lady K responded to Lady S:

    Yup, that is why you have to know where you are in life… When I dating mulitple men it was because I wasn’t looking for anything serious either. That’s just where I was then. However, life changes… I don’t regret AT ALL my dating experiences because it has lead me to know exactly what I want and how I want to feel in a relationship. The guys I dated were gentlemen…and I’ve maintained a friendship with some. I think once we have met someone that could be “the one” for you, it is hard to go back to old ways… but until then, dating can be fun!

  • Lady S said this:

    I agree! I didn’t always know what I wanted in relationships, but I was absolutely able to weed out what I did NOT want.

    I think as long as dating multiple people is not a secret to all parties involved, it can be healthy.

    But it’s when someone catches feelings that it can get complicated. And the fun goes right out the window, lol!

  • Lady K responded to Lady S:

    yeah, but for me those were normally men I could see myself with from the beginning and we just didn’t have the conversation. It’s rare that I fell for someone I just found cool and fun to be with. The problem is many of us don’t have “the right” conversations in the beginning to express how we feel. We feel it’s too early and don’t want to scare the other person off. So we sit back and say nothing hoping the situation will work itself out, um NO!!! (guilty).

  • I said:

    Thank you ladies for you comments and sharing. I myself never really dated and it has failed me and now I see the beauty and necessity in dating multiple people.