Dating Multiple Women - Advice Needed!

Prahasaurus
Prahasaurus Posts: 1,381 Member
So before you sharpen your pitchforks, let me explain... ;-)

For the past six months or so I haven't been dating that much, mainly due to my work and travel schedule. Recently things have changed, and in a big way. I've been on a few dates with two different women. Neither know about the other. I've never told either of the two that I want an exclusive relationship, and I haven't asked them if they are seeing other people. At the same time, I also haven't told them I'm seeing someone else. I'm not sure how they would take the news, probably not well... I get the impression that they both would probably welcome a more serious relationship.

The issue is that I like both of them, and I could see myself in a serious relationship with either of these ladies. But eventually I need to choose. And to do that, I need to get to know them much better. But I don't feel comfortable about the situation. I feel like I'm lying to them, or going behind their backs, even when we haven't said anything about not dating other people. And as I mentioned, I've only been on a few dates with each. Probably beginning around December. I just don't know them well enough, yet.

So how do I get to know them better, while at the same time not feeling like a total dog for "cheating" on them? And the entire process of getting to know them better implies more of a commitment from me. It's like a catch-22: commit in order to learn if a commitment can work. But what if I choose incorrectly?

Btw, both are similar: blonde (just a coincidence, I don't necessarily prefer blondes), around 35-40, attractive. Both have nice jobs. Neither has been married, neither has children. One had a boyfriend for a long time, and they recently broke up (six months ago). She's a school teacher, incredibly nice, beautiful, smart. The other focused on her career, is quite successful, witty, fun, but never found the right guy. They even have similar names, both beginning with "A," which makes text messages fraught with danger. :-)

How have others here handled this conundrum?

--P
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Replies

  • tangie82
    tangie82 Posts: 285 Member
    Unless you're bumping uglies with both, you shouldn't feel guilty. It's all a part of dating and there was no discussion of commitment. Have fun, get to know them. The rest should fall into place.
  • kristen6022
    kristen6022 Posts: 1,923 Member
    Are you asking if you can sleep with both to try out the merchandise before purchasing? The answer to that I'd say is no. There's no reason that you can't "experiment", but having sex with either or both in this situation I'd say is a big "no no". But others might not...I'm just old fashioned I guess.

    At this point you don't need to tell them about each other but you do need to respect their health by not dipping your stick everywhere you see fit. Don't take more than 2 months of "getting to know them" before deciding between one or the other - leading them on for long periods of time will only lead to both of them skedaling and you being left with neither of them.
  • Prahasaurus
    Prahasaurus Posts: 1,381 Member
    Unless you're bumping uglies with both, you shouldn't feel guilty. It's all a part of dating and there was no discussion of commitment. Have fun, get to know them. The rest should fall into place.

    Not both. :blushing:

    Interesting euphemism, btw.

    --P
  • tangie82
    tangie82 Posts: 285 Member
    Unless you're bumping uglies with both, you shouldn't feel guilty. It's all a part of dating and there was no discussion of commitment. Have fun, get to know them. The rest should fall into place.

    Not both. :blushing:

    Interesting euphemism, btw.

    --P

    Oh you man *kitten*. Just kidding. This is probably why you are feeling guilty. Make a choice mister.
  • tangie82
    tangie82 Posts: 285 Member
    Are you asking if you can sleep with both to try out the merchandise before purchasing? The answer to that I'd say is no. There's no reason that you can't "experiment", but having sex with either or both in this situation I'd say is a big "no no". But others might not...I'm just old fashioned I guess.

    At this point you don't need to tell them about each other but you do need to respect their health by not dipping your stick everywhere you see fit. Don't take more than 2 months of "getting to know them" before deciding between one or the other - leading them on for long periods of time will only lead to both of them skedaling and you being left with neither of them.

    ^^ yep what she said.
  • Prahasaurus
    Prahasaurus Posts: 1,381 Member
    Are you asking if you can sleep with both to try out the merchandise before purchasing? The answer to that I'd say is no. There's no reason that you can't "experiment", but having sex with either or both in this situation I'd say is a big "no no". But others might not...I'm just old fashioned I guess.

    At this point you don't need to tell them about each other but you do need to respect their health by not dipping your stick everywhere you see fit. Don't take more than 2 months of "getting to know them" before deciding between one or the other - leading them on for long periods of time will only lead to both of them skedaling and you being left with neither of them.

    Firstly, it's not about permission to have sex with either or both of them. This is serious, it's not about sex... :-)

    In the spirit of openness and internet anonymity, I should say I have slept with one of the ladies on our first date. And also on our third date - the second date was lunch. ;-) The first instance wasn't really planned, it just involved the perfect alignment of the stars, and way too much alcohol... :-)

    As to health, I'm usually quite good about always using a condom. I would not sleep with multiple women casually and put anyone's health at risk.

    By the way, the nature of one of the lady's job (travel agency) is that she travels a lot for extended periods of time, and she left about a week ago for an assignment. She won't be back until early January. We communicate every other day or so by sms. So it's not like I'm seeing one on Friday, the other on Saturday. Not sure if that's relevant info, however...

    --P
  • kristen6022
    kristen6022 Posts: 1,923 Member
    Dude, not judging. You can do with your equipment what you want. I was just telling you what I'd prefer to happen to me if I was in this situation (and I have been, with my best friend, but that's a whole other ball of wax all together). So, since "bumping uglies" with Lady #1 are you wanting to "try out" Lady #2 to see if she's better then if she is you'll drop Lady #1? Which lady do you feel a stronger non-sexual connection with? Because we all know, sex isn't everything and maybe you don't need to try out both of the merchandises before you buy it? Are you feeling a pull to Lady #1 because you've been in bed with her? Or are you not sure if she's compatible and you are feeling guilty about sleeping with her?

    I only probe because you must be "torn" if you are coming on here and letting us dissect your love life? LOL
  • Prahasaurus
    Prahasaurus Posts: 1,381 Member
    Dude, not judging. You can do with your equipment what you want. I was just telling you what I'd prefer to happen to me if I was in this situation (and I have been, with my best friend, but that's a whole other ball of wax all together). So, since "bumping uglies" with Lady #1 are you wanting to "try out" Lady #2 to see if she's better then if she is you'll drop Lady #1? Which lady do you feel a stronger non-sexual connection with? Because we all know, sex isn't everything and maybe you don't need to try out both of the merchandises before you buy it? Are you feeling a pull to Lady #1 because you've been in bed with her? Or are you not sure if she's compatible and you are feeling guilty about sleeping with her?

    I only probe because you must be "torn" if you are coming on here and letting us dissect your love life? LOL

    It's not about "trying out" anyone for sex. Not sure why you're focused on the sex. It's about getting to know someone properly. Who they are, what they want out of life, what they believe in, etc., etc.

    Although I admit the fact I've slept with one probably does add to the guilt, and complicates the process. And perhaps this is why I feel I need to resolve this asap. I probably couldn't sleep with both at the same time.

    But I fear this thread will now be hijacked by the sex issue, when to me it's more about how to properly get to know someone without committing, and especially how to do that when dating multiple people. The sex is only one part of this, and not for me the most critical part.

    --P
  • kristen6022
    kristen6022 Posts: 1,923 Member
    I didn't mean to make it about sex, but really the only reason you should feel guilty for dating 2 women is the sex part. Dating multiple people at one time really isn't a problem if you haven't told them you are seeing them exclusively. Like I said before, I wouldn't let it go past 2 months total with out making a decision (if you want a serious relationship, if you don't, date 100 women at one time, no guilt with that. But if you are thinking one of these lucky ladies will be your girlfriend soon, treat both of them the way you'd treat your sister or best friend (or at least would want the person they are dating to treat them) so that when you get into a relationship with one of them you have nothing to explain, feel guilty about or confess. Straight up honesty is the best policy. If you get to the 2 month mark and you still haven't made up your mind, I suggest coming out and telling them you are dating other people, so they know and they can make the best decision for themselves.
  • MissingMinnesota
    MissingMinnesota Posts: 7,486 Member
    The one that works for the travel agency, if in a serious commited relationship with her would you be okay without seeing her for extended periods of time? It seems like you are right now but it is the early stages, will you be okay with that in the long run?
  • Danielle_2013
    Danielle_2013 Posts: 806 Member
    This sounds like an episode of the Bachelor...minus the screaming and hair pulling mind you.

    Interesting challenge. I think most women, or people, want to believe they are special. I know that people do multiple date...but if I found out that someone wasn't wholly focused on me I would be disappointed and think less of our potential connection. Then again, my ego can be a bit of a problem! I am a hypocrite also, as I have balanced dating multiple men. Just never let them know and you have to be quite careful with text and scheduling. I will say though, deep down I always knew who or what I wanted or might work for me...even if just a hunch. It eventually gets to a point where you do have to choose...I like having say..a two month limit on things.

    I guess in figuring this out I would ask myself a number of questions...who do you feel more drawn to, who can't you stop thinking about? When you do go on dates...ask ALL the big questions...don't hold back. For whatever reason, maybe because I am slightly intense, I always find myself having non-first-date kinds of conversations with people I date or relative strangers. It is fun...cuts through crap and really lets you know if you are on the same page.
  • SVCat
    SVCat Posts: 1,483 Member
    I would continue dating both until I had a clear idea of who the ideal mate is. Just be careful not to make both of them fall in love, I would feel like a jerk if I had to break a heart. It appears as if both of them are lovely women and neither deserve to be treated unfairly. From the tone of your messages, sounds like you're trying to do what is best. I think your moral compass is pointing in the right direction.

    Good luck to you sir.
  • jenbit
    jenbit Posts: 4,252 Member
    Maybe its just me but I don't see the big deal. Like you said your not in a committed relationship with either of them so that right there implies that you are dating more people. Wether your having sex with one, both or 53 people its really not anyones buissness. Now you may be feeling guilt because you like both of them and thats understandable. What you need to do is figure out which one you like more. But there is nothing wrong with dating them both until you find out which one you like more
  • dbrightwell1270
    dbrightwell1270 Posts: 1,732 Member
    I think it's a difficult situation and the thought of choosing incorrectly is inevitable. One thing I would consider is how relationship ready either or both of these women are. One was in a LTR that only ended 6 months ago. There is usually an I'm lonely/ I'm not used to being on my own/ I question my own self worth (whatever you want to call it) phase. She could seem very interested in a relationship and truly believe in her heart that she is but when the chips are down, she may bail because it is too much and she needs more time reorienting herself to singledom. If she's the one you had sex with and she is still coming around, it is less likely that she is going to bail if you decide to be exclusive with her. She is also the one who is more likely to be hurt if you decide you want to be exclusive with the other one.

    The second girl should probably be more accustomed to the dating world. Never finding the right guy could be caused by a lot of factors but if she is reasonably attractive and hasn't had any LTRs to speak of, you have to ask why. If she is the one you had sex with, there is a decent chance that she is just enjoying the ride (no pun intended). She may or may not be looking for something exclusive.

    This is really what I hate the most about dating. There is just so much inevitable game playing or manuevering because of asymmetric information. It's easy when you go an dates with a few people and you don't click. It's easy when one clicks and the rest do not. It's confusing as hell when you meet multiple that seem like good matches but none stands above the rest. I've never successfully managed it so I can't give any sound advice. One thing to consider is that neither stands above the other because both are functional but neither is really all that exceptional. Good luck to you.
  • JanieJack
    JanieJack Posts: 3,831 Member
    I’ve never understood how guys expect us to believe they care about a woman’s feelings regarding “getting to know different women” if they’re sleeping with multiple women. Dating multiple women is one thing, and I highly recommend it, but sleeping with them is another. Even in this day and age of more common FWB acceptance, most women I’ve talked to think that sex = “we’re exclusive now.”

    If you really want to get to know multiple women without hurting their feelings (vice just trying to brag about getting some to a group of singles) then don’t sleep with them. Just get to know them by going on dates and reserve the bedroom for the one you choose.

    Oh.. and what Dave said:
    One thing to consider is that neither stands above the other because both are functional but neither is really all that exceptional.
  • poncho33
    poncho33 Posts: 1,511
    Date them both for awhile. I see no reason why you couldn't stretch this a couple of months until you figure out which is the one for you, if either. You travel a lot, so just explain to them that your time is limited and this should by you time from having to commit.

    As for the bumping of the uglies, who cares if you're doing them both... you're a guy and that is your birthright!! :wink:
  • 4themoney
    4themoney Posts: 797 Member
    mars and venus on a date addresses this kind of situation.
    apparently there are stages of dating and you are supposed to move through them in order, to figure out if you want a serious relationship with someone. and part of the stages are moving into exclusivity...... which is where you are.

    the girl that you have slept with already, do you feel like you owe her more because you've slept with her? or are you feeling like you like her more because you did?

    in the stages to a committed relationship, sex isn't supposed to come until AFTER exclusivity. mainly because it skews our feelings and emotions.

    so, if i were giving you advice, i would tell you to tell them both that you are dating other people. both of them could be thinking that things are getting more serious between the two of you and you're moving towards being exclusive. but, since you're not on the same page exactly ( right now) it might help them to sort out their feelings too. OR, i would suggest making a pro and con list for each woman and then breaking it off with one and moving towards exclusivity with the other. not saying this book is the " ulimate guide for all things" but, if you follow his advice then it's easy to see why it's hard to focus on ONE person when you're dating more than ONE person......

    he says initially it's ok, but after there is attraction and interest ( and a couple dates under your belt) you need to focus on ONE and move forward with her. don't be afraid that you are making a wrong choice. you are interested and attracted to both of them :-)
  • SVCat
    SVCat Posts: 1,483 Member
    I’ve never understood how guys expect us to believe they care about a woman’s feelings regarding “getting to know different women” if they’re sleeping with multiple women. Dating multiple women is one thing, and I highly recommend it, but sleeping with them is another. Even in this day and age of more common FWB acceptance, most women I’ve talked to think that sex = “we’re exclusive now.”

    If you really want to get to know multiple women without hurting their feelings (vice just trying to brag about getting some to a group of singles) then don’t sleep with them. Just get to know them by going on dates and reserve the bedroom for the one you choose.

    Oh.. and what Dave said:
    One thing to consider is that neither stands above the other because both are functional but neither is really all that exceptional.

    Janie...I disagree. First of all, the man has already said this isn't about sex. He is not a bad looking man, I'm sure sex isn't hard to come by if that is all he wants. He already said things just naturally progressed with one of them. Tthat being said, they are all consenting adults. It's a two way street, these ladies aren't being forced onto the "bed".
  • jkandktmom
    jkandktmom Posts: 1,010 Member
    I’m completely heat broken. :brokenheart:

    I understand that your real question is how to get to know both of them more without increasing your involvement. However, I think you may know the answer you just don’t want to hurt the other on that is a “pretty good” choice.

    When you go to sleep at night what is the last thing on your mind? When you think of a perfect day who are you with? Most importantly if they both broke up with you tomorrow how would you feel?
  • JanieJack
    JanieJack Posts: 3,831 Member

    Janie...I disagree. First of all, the man has already said this isn't about sex. He is not a bad looking man, I'm sure sex isn't hard to come by if that is all he wants. He already said things just naturally progressed with one of them. That being said, they are all consenting adults. It's a two way street, these ladies aren't being forced onto the "bed".

    This is funny to me, because when *I* was dating other guys while getting to know BB, NOT ONE man on this site supported me. Every single one said I was being a jerk… and I wasn’t sleeping with ANYONE.

    It’s a free country and we can all disagree… I’ve just seen more guys (than not) say “we’re all adults” but at the same time don’t tell women they’re sleeping with others because they know she will usually move on.

    If P is seriously asking how to proceed, then my advice is no more sleeping with them until a) he’s sure which one he prefers or b) whoever he’s sleeping with is ok with him sleeping around and understand that “this doesn’t mean we’re exclusive.”

    We can say all day “we’re adults” but if this progresses much longer (it’s already been a few weeks) then the women may get hurt. If he cares about a possible relationship with either of them it wouldn’t matter. But if one of these girls is a long term possibility, it just might.
  • SVCat
    SVCat Posts: 1,483 Member

    Janie...I disagree. First of all, the man has already said this isn't about sex. He is not a bad looking man, I'm sure sex isn't hard to come by if that is all he wants. He already said things just naturally progressed with one of them. That being said, they are all consenting adults. It's a two way street, these ladies aren't being forced onto the "bed".

    This is funny to me, because when *I* was dating other guys while getting to know BB, NOT ONE man on this site supported me. Every single one said I was being a jerk… and I wasn’t sleeping with ANYONE.

    It’s a free country and we can all disagree… I’ve just seen more guys (than not) say “we’re all adults” but at the same time don’t tell women they’re sleeping with others because they know she will usually move on.

    If P is seriously asking how to proceed, then my advice is no more sleeping with them until a) he’s sure which one he prefers or b) whoever he’s sleeping with is ok with him sleeping around and understand that “this doesn’t mean we’re exclusive.”

    We can say all day “we’re adults” but if this progresses much longer (it’s already been a few weeks) then the women may get hurt. If he cares about a possible relationship with either of them it wouldn’t matter. But if one of these girls is a long term possibility, it just might.

    It's a two way street, I dont' see anything wrong with playing the field and finding the best mate. I would have approved of you being a "Jerk" ; )
  • afv417
    afv417 Posts: 466 Member
    I think it's a difficult situation and the thought of choosing incorrectly is inevitable. One thing I would consider is how relationship ready either or both of these women are. One was in a LTR that only ended 6 months ago. There is usually an I'm lonely/ I'm not used to being on my own/ I question my own self worth (whatever you want to call it) phase. She could seem very interested in a relationship and truly believe in her heart that she is but when the chips are down, she may bail because it is too much and she needs more time reorienting herself to singledom. If she's the one you had sex with and she is still coming around, it is less likely that she is going to bail if you decide to be exclusive with her. She is also the one who is more likely to be hurt if you decide you want to be exclusive with the other one.

    The second girl should probably be more accustomed to the dating world. Never finding the right guy could be caused by a lot of factors but if she is reasonably attractive and hasn't had any LTRs to speak of, you have to ask why. If she is the one you had sex with, there is a decent chance that she is just enjoying the ride (no pun intended). She may or may not be looking for something exclusive.

    This is really what I hate the most about dating. There is just so much inevitable game playing or manuevering because of asymmetric information. It's easy when you go an dates with a few people and you don't click. It's easy when one clicks and the rest do not. It's confusing as hell when you meet multiple that seem like good matches but none stands above the rest. I've never successfully managed it so I can't give any sound advice. One thing to consider is that neither stands above the other because both are functional but neither is really all that exceptional. Good luck to you.

    I completely agree. No need to write this over. :)

    I will add that it is ok, in my book, to continue dating both as long as you don't get too involved. It's easier said than done because I don't think I could. If you feel more for one than the other you may just have to be upfront about it and date that one. Unfortunately that's the world of dating. I hate the mix of feelings and emotions too and having to test one over another... I do believe that everything happens for a reason... listen to your heart, to your gut and your instincts.

    Good luck!
  • kristen6022
    kristen6022 Posts: 1,923 Member
    I think everyone here has agreed that you will need to put a time limit on seeing both if you feel you might end up with one of them long term.

    No, no one was "forced" into bed, but MOST women think sex means there could be a future. It's the way of the world guys.

    And I know you don't want it to be about sex, but if sex is being had, it kinda is about sex. I wish it wasn't, but more than likely the one you have slept with will have developed deeper feelings for you than the one that hasn't had the chance.

    I agree with Janie, I know that you have had sex with the one already, but I think until you have made a decision to be with one of them, no more sex with either.
  • Is the one you are sleeping with the one that is 6 months out of LTR? I am wondering if she is just in the post relationship "fun" stage and isn't really looking for a boyfriend. You won't know unless you have that conversation, but that was my first thought.
  • TheKitsune6
    TheKitsune6 Posts: 5,798 Member
    Do you know what they want out of it? Have you had a talk about exclusivity and what they want? Have you TALKED about sex, the things they like? Frequency? See if that matches up.

    The way you word it, it's almost like you are dating clones that have slightly different lives. If that's the case, flip a coin. Really until then just keep talking to them about things that are meaningful (not the weather) until you find something you really like, or something you don't. Eventually those discerning facts will be what enables you to make your decision.

    In the meantime, sex or no sex, as long as they know you aren't exclusive with either of them I don't see a problem with dating two girls at the same time. Just make sure that she understands that sex does no equal a relationship. I might be alone in that but even if one of the gals does get hurt she probably won't be scarred for life - unless she's really fragile and then in that case you dodged a bullet.
  • AnnaPixie
    AnnaPixie Posts: 7,439 Member
    Personally, I dont get the multi dating strategy! Hedging your bets in love just seems very cold to me. Plus, I could only focus on one person at a time and give them all of me.

    I would just carry on seeing the one you are sleeping with and if it doesnt work out, then contact the second one in X weeks/months time. I don't see why getting to know them has to be simultaneous. Your decision will just become more difficult as time goes on! If you see one, and you're thinking about the other, then you obviously dont want the one you're seeing!
  • JanieJack
    JanieJack Posts: 3,831 Member
    Had some interesting PMs on this topic. One of our guys pointed out that in his experience, a woman isn't really wanting a relationship if she sleeps with you quickly.

    In my little bubble of culture, a man almost never wants a relationship with someone he sleeps with that quickly. If a woman wants a relationship she, knowing the stigma that "some guys" attach to DTD too soon, will hold off on sex for awhile (even if she really wants it).

    However, this forum has introduced me to many women (and men) who would DTD on the first/first couple of dates, so I guess I’ll adjust my advice to align with Kit: Find out what they want and make sure everyone’s expectations are aligned (i.e. don’t lie to them).

    @Anna… do you think if he focused on #1, then tried to contact #2 when that fizzled would #2 be offended and cross him off the list…? I know everyone is different. I, personally, would be more offended by him breaking contact and then coming back later than I would be if he were getting to know us both at the same time.
  • RunIntheMud
    RunIntheMud Posts: 2,645 Member
    My thoughts...

    One is out of town for a little while, so use that time to get to know the other. I'd say devote this time to the woman here and then devote some time to the other woman next week when she gets back. Make sure your relationship expectations are the same and just see who you're more interested in.

    And, in regards to having sex so quickly...men and women do it. Sometimes things happen. It doesn't mean that either of them don't want a relationship. And, just because a man waits a short while that does not mean the man does want a relationship. Sex happens. But, the moment I think about, or have sex with a man, is the moment that I stop talking with other men.
  • AnnaPixie
    AnnaPixie Posts: 7,439 Member
    @Anna… do you think if he focused on #1, then tried to contact #2 when that fizzled would #2 be offended and cross him off the list…? I know everyone is different. I, personally, would be more offended by him breaking contact and then coming back later than I would be if he were getting to know us both at the same time.

    Like I said, I dont get the multi dating concept. If I like someone, I give the relationship 100%. I would not double date and would not want to be double dated!! So, no, I would much rather be contacted later on by a guy that was serious about getting to know me 'only'. Not someone that was weighing up his options simultaneously.

    Bear in mind that this is gone beyond the 2 or 3 dates so inevitably, the sex is going to happen with both women. I think after 2 or 3 dates you KNOW if want a relationship. And as the OP has said, he likes both women. I can only see the decision getting harder and more complicated and turning into a big cheating affair! I'd rather he blew me off after 3 dates and picked up later (not saying I need to know why!!!), than tossed me aside after a couple of months when I'm emotionally and physically invested.

    ETA Obviously if the dates were purely platonic fact finding events, then nobody will be getting involved. But, I think the OP knows that it's gone beyond that stage..........
  • christine24t
    christine24t Posts: 6,063 Member
    I think everyone here has agreed that you will need to put a time limit on seeing both if you feel you might end up with one of them long term.

    No, no one was "forced" into bed, but MOST women think sex means there could be a future. It's the way of the world guys.

    And I know you don't want it to be about sex, but if sex is being had, it kinda is about sex. I wish it wasn't, but more than likely the one you have slept with will have developed deeper feelings for you than the one that hasn't had the chance.

    I agree with Janie, I know that you have had sex with the one already, but I think until you have made a decision to be with one of them, no more sex with either.

    Agree 100%.
    Sex clouds judgement.