Hey Sasha,
I have a question for your readers. I’m having a moral dilemma of sorts. Do you think it’s alright to date two women at once? I’ve never been in this position before and I’m not sure what to do. I can honestly say I like both equally but I don’t know either well enough to know if it will lead to anything serious, which is why I want to keep both for the time being. Since no one has said anything about being serious I figure it’s okay, but I don’t want to get away on a technicality and then be called a cheater. What do you think? All is fair when you’re single or is this cheating?
OK, so this is sort of a juicy question and one that I will gladly give you my two cents on and then open the comments to our lovely readers.
I don’t think there is anything wrong with dating two women at once, as long as neither one of them thinks that you’re exclusive with them. Being single is called SINGLE because you’re not committed to any ONE person. When you are, you are no longer single.
I know a lot of people have a problem with this and I don’t get why. Back in the stone age when I was single I dated more then one person at a time, consistently. In fact, I believe my record was juggling 5 women at a time. Did they all know about each other? No. But was I cheating? NO!!!! Why? Because I was SINGLE!!!!!
When you’re single is the time that you get to explore what makes you happy, what turns you on, WHO turns you on. Being single is the only time you will ever get the chance to be selfish about what YOU want and make no apologies for it.
Anyone that whines about this, doesn’t really understand the differences between “dating” and being in a committed relationship. Because granted, unfortunately there are a lot of people (men and women) that assume that 3 dates = exclusivity or that because they aren’t dating anyone else, you shouldn’t be either. Which is BULLSHIT and this is where the art of communication comes in.
I call it an art, because when done right, will actually allow you to be true to yourself and honest with those that are in your life.
I am not advocating acting like a total douche bag and playing games with girls hearts. Be honest with them. If they ask if you’re seeing someone else, tell them the truth and then let them decide if they still want to date you or not.
But … and here is where I’m going to get in trouble …. if they don’t ask, you don’t really have to volunteer that information either. I think it’s called plausible deniability?? LOL … no really. Because later, when the shit hits the fan and let’s face it, when you’re lying by omission, you’re treading some very grey water here. If she blows up on you the day she finds out there are other women, you can always claim, “But baby, I thought you knew?! I mean, I just assumed you were dating other people too since we never talked about it.”
OK, yes, that is a major player dick head move. Am I guilty of it? How do yo think I know what to say? But does it work? Yes. Sort of. If she’s really into you, it might get you a second chance with her. But be warned at this point, you will have to tell her if she’s not the only lady in your bed.
So to sum it up. Is it OK to date two women at once when you’re single? Yes, because if you think about that question, that’s actually the ONLY time it’s OK. So go for it. But be prepared to be honest if either one of them starts asking the hard questions.

I agree with Sasha. Although on a personal level it gets super sticky when they know about each other. And incredibly catty
Yep, you are definitely single until you make a commitment with one person. Have fun!!
Sasha, as usual, I agree with everything you said. It’s perfectly OK to date more than one person, just as long as you are upfront about it when they ask you. I would probably make it clear that I was dating others before they asked, just so they wouldn’t get it into their heads they were the only ones, that we were a “couple”, or that I was her girlfriend. I believe in full disclosure to be fair. The people you are spending time with deserve to be able to choose whether they want to date someone who they aren’t exclusive with. Being open and honest will enable you to not feel guilty, and you won’t be giving a wrong impression to the women who can blame you for their hearbreak because you led them on. You shouldn’t reveal the identities of the others on your social calendar, but you should tell how many others are in the picture. If anyone chooses to continue dating you after you’ve made this information truthfully available, it shifts the responsibility from your shoulders onto theirs. If they get their heartbroken, there’s no one to blame but themselves. Some may prefer to spend casual time with you and put intimacy on hold until you can committ to an exclusive relationship. It doesn’t bother some to be “one of many”, but it might really bother others if the person they’re having sex with is sleeping around. If you’re not an asshole, you will strive for equality in power, and keeping this information secret (if asked) takes power away from those you are dating. A lot of men are guilty of this, and I hope women would treat eachother better and with more respect. Happy tails to you.
As a dedicated (but reasonable, or so I tell myself
) libertine, I can only second what the others have said. As long as you do not make any promises, and everyone involved is aware of how, shall we say, uninhibited the arrangement is. Of course, that does not mean you have to tell them when, where and with whom you are – less detailed information (as in: “you are not the only person I’m dating”) should suffice.
Were I to write a guide on avoiding drama, the first rule would state: “your terms should be clear from the start”. Just my two redundant cents.
Have fun!
I agree with Sasha on this one. You can totally date two women at the same time, and do it with class, as long as they both know you aren’t exclusive. I also agree that there is a difference between “dating” and “commitment/exclusivity.”
I never had any issue with it, but it was because from the start I was honest. It was fun, and it also gives them the freedom to do the same. Remember that, if you are okay with dating others…you need to be okay with them doing that too.
Dating, to me, is like scouting for that perfect fit. But, dating more than one person isn’t an excuse to be a douchebag, take calls from other girls when you are on a date, or be inconsiderate, hurtful, or rude. Remember, this could be a person you end up with!
For me, though I am happily committed to my girl, I am so very glad that I found out what I *didn’t* want, and really felt like I knew what was out there. I’m a better person for it, and I think I appreciate what I have far more.
I concur with Sasha. If you havent talked about/decided you are “relationship” status, you are simply datin-and single. It’s kind of like (this sounds bad) like grocery shopping. Your browing the different merchandise to see what you want. No matter how many dates you’ve gone on or what you’ve done, if you haven’t talked and mutually decided that you are exclusive than you’re fair game.
I see it as ok as long as you are not giving anyone involved the impression that you are exclusive. Make it very clear that you are still on the market but you want to see where it goes. Many people automatically assume that if you are dating, you are exclusive. I made the mistake of assuming that myself before and it lead to heartbreak. So I think you should make sure your intentions are clear in a situation like this.
Ah but heres another scenario, say someone is married and wants a relationship with someone who is also married with both of their partners knowing? what about that?
Is it just me, or is omitting certain things equivalent to lying. I know if my gf just so happened to skip out on telling me a certain part of her day (that she knew I would be upset about), it would be just as hurtful as if she lied to me.
Personally, I don’t like dating more than one person at a time – because I want to dedicate my time to that one woman, focus and figure out if she is right for me. However, I do wish I could date multiple women at the same time, because like you said being single means its your time to explore what makes you happy…
difficult!
Honesty and open communication are critical. (Jaz steps onto soapbox) To repeat the critical concept that I always tell everyone (every the teller at the bank who later told me she followed my advice
) so again people be very careful who you date when you’re in your 23 to 32 age range that
is the easiest/best/main age group to meet what can lead to long term/life long couples
tend to meet. Good luck it will all work out.
And just to prove my point that the shit will hit the fan, if you neglect to tell her you’re dating other people: when Remi read this, it started a conversation about EXACTLY how many other girls I was dating when we first started dating.
She KNEW of one other, main one. And one other “complicated” situation. However, this morning I was caught off guard telling her about this blog and forgot I had never told her the entire story. So after a little bit of a heated discussion, it came out I was “dating in the broadest sense of the word” a few extra girls at the same time. So 4 years later, after she put a ring on it, it still got me into trouble for not being up front!!
So heed my warning …. Just be honest. But I stand my ground, don’t be too specific. A simple, “I’m dating other people” should suffice. Have the detailed conversation only when absolutely nessary.
Remi did tell me today that had she known EXACTLY HOW MANY women I was dating at the time we would have, and I quote “had a lot more problems.”
Snerk… Lmao. xD
@Cassie, I’m totally with you on that! Omission of some things= lying to me.
@Sasha, um first off, I’m sorry but LOL!!!
Clearly the statute of limitations does NOT apply to relationships! Also, I’m now single and would love to know how you managed to date several women all at once… seems like a good skill to acquire.
Hey, so I’m the one that emailed in the question to Sasha. I wanted to say thank you all for the responses! So far its been working out pretty well but I can see this becoming an issue in the future. I just don’t see how people date more than 1 person for a long period of time. For a little while sure, but after a certain point I think I’ll have to make a decision.
Omission is certainly tricky. I guess until one of them goes in for “the talk” I’m in the clear. How long can you keep that up though until one finds out and gets royally pissed off?
Dear Single: I wish you the best. The answer to your question obviously lies in the women you are dating. If you were dating me, and I wanted you all to myself, that answer would be,”not very long”. If I was just dating you for something to do to keep myself from being bored, the answer would be, “until you got tired”. You just never know. Your lovelies may also be juggling multiple dates, in fact, if I were you, I would assume they were until you find out differently. I guess you’ll know when you want to go exclusive with one of them when that idea starts to bother you.
I tend to run towards monogamy pretty quickly. I started dating someone last year while talking to about 5 others (literally, talking to) and when I realized I liked that one woman, I pretty much quit talking to all the others. Mistake! She and I lasted a month, and then I lost a chance to get to know and possibly date the others. I’m not too upset about it because I wasn’t THAT into the others, but still, I should have kept talking to them and figured out a way to tell them I started seeing someone I liked.
Oh, and the one I dated for a month? I made the stupid move of getting upset when she admitted to having been on dates with others when we hadn’t even discussed exclusivity.
So, in a word – learn from my dating mistakes. Keep communication open, date as much as you’d like and until you’re with someone you realllly want to be exclusive with AND you’ve had the talk, you’re not cheating on anyone.
Ps. The reason I got upset was because I REALLY liked her and may have let my imagination get away from me (see some of my prior blogs on here).
I agree with Sasha and Rexie and yet in the UK we seem to have very different rules. We don’t so much ‘date’ here as get together. You wouldn’t really ask someone out on a date, and you definitly wouldn’t if you’d only just gone out with somone else. I think we need to take a much more laid back approach to the style of dating and say if you’re single, you’re allowed to see as many people as you want!
This is a good topic. I appreciate everyone’s input. My situation is I AM stuck on one person who has only been out with me once. If she wanted to spend more time, I would go exclusive with her. But in the meantime, I do feel it would be healthy, shall we say, for me to see other people, so I don’t put my life on hold. Even though I feel, she is worth waiting for. I don’t think I’m going to find a better person for me, but hey, I could be wrong, and I won’t know until I put myself out there and try to find out. If my first choice does come around to my way of thinking, though, how will I handle her curiosity about whether I’ve been seeing other women. I guess I shouldn’t worry about the future, it’s just: I wouldn’t want to lose her over that. I can see how all this could become a big dillemma for many of us, and BTW, I would love to have a different date every night for a while, just so I could think about something else, other than her all the time. Thanks for opening this topic.