When Is The Right Time To Choose Between Two Amazing Men?

When Is Right Time To Choose Between Two Amazing Men?

I am in a quandary and I am hoping you can help. Last month, I wrote to two men that I was very interested in. The good news is that both of them wrote me back and I have been seeing both for the past 2-3 weeks. Things have been going well, and I give a lot of credit to what I have learned from your book, emails and this site. However, this is not something I have ever done before and I am having a hard time with the idea of juggling.

The problem is that I really like both of them and they both seem to be really amazing guys. They follow up, they text, we talk, make plans…it’s all good. I am lucky. On the other hand, I don’t know how to manage this. I know I need to make a decision before things go too far (becoming too physical), but how do I know when? I am trying not to let things move too fast physically or emotionally, but they both seem very interested and I just don’t know what to do.

Making a decision about a guy is no different than any other decision. You weigh your pros and cons, you do your cost-benefit analysis, you use a little logic and a little emotion, and then make a largely arbitrary choice without knowing if you’re right.

Many people may not see this as being a true problem. But I don’t know how much to say to these men, or not say because it’s so early in the relationship. They seem to be feeling pretty strongly so I feel some pressure to figure this out.

I searched the blog to see if you’ve addressed this before but haven’t found quite the same thing. Any help you can provide would be so appreciated.

Thank you,

High quality problems, indeed.

So, Maggie, you’re seeing two great guys for 2-3 weeks. You didn’t give me any identifying information that would allow me to recommend one man or the other, so all I’m left with is the general idea of dating multiple men simultaneously. The good news: because of the broad scope of the question, every reader who is interested in deciding between two men can use this advice. The bad news: without more specific details, I’m not sure you can.

Regardless, I’m going to do what I always do in these situations: insert myself in the middle and riff a little bit.

1. Making a decision about a guy is no different than any other decision. You weigh your pros and cons, you do your cost-benefit analysis, you use a little logic and a little emotion, and then make a largely arbitrary choice without knowing if you’re right.

I recall one time that I was dating two women simultaneously for about a month. Both were cute, smart, cool, late 20’s, Jewish, and interested in me. And while I was hooking up with (not sleeping with) both of them, something didn’t feel right. I couldn’t act silly around them. I couldn’t let down my guard around them. I didn’t LOVE being around them. My ambivalence was a feeling, more than a logical choice. Which is why I kept looking around on JDate for that entire month that I was seeing both of them. One woman even called me on it — “How dare you get online after our great date?” but I didn’t flinch. It was my right to look for other women if I didn’t feel I could commit to her. Just as it’s her right to keep her options open until she finds a boyfriend-worthy man.

As it turns out, I met a third woman, who was so incredible that I immediately emailed the other two, broke things off, and took my profile down to commit. Naturally, it took the third woman about two weeks to feel comfortable committing to me, but she eventually did.

This is a somewhat complicated (but typical) example of how dating works. It’s every man for himself. And neither party is under any obligation until both parties agree to commit to each other.

Which brings me to a very important point:

2. Your choice is not binary, nor is it permanent. Yes, you’re dating two men, but that doesn’t mean that these are the only two men on the planet.

Let’s say Bachelor #1 turns out to be a great guy…who admits after a month that he never wants to get married or have kids. You do.This conversation is over. You agree to be exclusive with Bachelor #2.

Let’s say Bachelor #2 turns out to be a great guy…who admits after two months that although he was excited about you, he’s on the rebound, not emotionally over his ex-girlfriend and is not fit to be your partner at this point in time.
What does that say about you, men, or dating?

Yes, you’re dating two men, but that doesn’t mean that these are the only two men on the planet.

Nothing! All it tells us is that…

3. Time reveals all.

You may not know the front-runner for the open position of “boyfriend”, but since you’re the CEO of Maggie, Inc, you’re going to take your sweet time to see how the interns perform in a limited capacity. The faster they follow up, the more work they choose to take on, the quality of their performance — all will start to differentiate these two men to make your decision a lot easier. You’ve never heard of a woman standing on the altar with two men, have you? Exactly.

Everyone figures this out, eventually. And finally…

4. Physical intimacy is a personal decision.

For me, I decided back in 2004 that I wouldn’t sleep with anyone who wasn’t a girlfriend. I stuck with that and avoided breaking a lot of hearts. In general, I think this is the best policy, because it’s a clear dividing line that any man can understand.

“I only sleep with boyfriends, and until we figure out if an exclusive relationship is the right course of action for both of us, we’re gonna have to just stick with some incredible foreplay!”

Only you can determine whether you can have sex with two guys simultaneously without a commitment to either of them. But I wouldn’t recommend it. Either you will get attached or THEY will get attached — and since you haven’t figured out your feelings yet, I would think that attachment is something you’d want to avoid.

I predict that by the time you read this, Maggie, everything will have sorted itself out. So please come back and let us know if I retroactively steered you in the right direction, okay?

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  1. 1

    Wow, seems like a sweet deal to be Evan! Everywhere you went you just magically kept finding great women who were into you and wanted to date you! You had the leisure of committing to someone before they committed to you because you always just assumed that so many women wanted to be with you that you could always get what you wanted. Yes, I’m being a little tongue and cheek here – success in any arena should be celebrated, not resented – but I really don’t think you understand the average person’s dating experience.

  2. 2
    Evan Marc Katz

    This is called confidence, Jenna. That’s why I get to do this job. When you carry yourself with confidence, you assume that people will like you and you don’t accept crumbs out of fear you can’t do better, yes, it’s a sweet deal. But it’s a sweet deal that anybody can have.

    1. 2.1

      Yes, but you’re a man and I guess from reading a lot of dating blogs, women “dig” confident and commanding and personable men. I think the criteria for men is more looks, looks, looks – at least in deciding who to ask out and date. Confident and personable comes later when they (the men) decide whether or not to keep dating with a relationship in mind.

    2. 2.2

      I would totally agree with Evan here, when you don’t accept anything less than what you deserve, keep following your lifes best things, and move with confidence, more people do come.
      They don’t when you make them feel you’re dependant on them in any way or that you don’t have balls enough to break it when its time.

    3. 2.3

      I can actually attest to that. A week ago I had no prospects, I was feeling crappy and insecure. Fast forward to a few days ago where I just decided, “You know what, I’m pretty damn awesome,” and I started thinking with an abundance mentality, and now I’m have two awesome guys chasing after me.

    4. 2.4

      Agreed! I know my worth and I project confidence always and amazing things happen! It’s amazing what happens when I just smile even. I have been meeting men like crazy and have even gotten to the second and third date with most, but just don’t want to committ out of loneliness or convenience. I love all your advice Evan; it truly does work!

      1. 2.4.1

        I whole whole-heartedly agree!   When I read that Evan didn’t flinch when that woman was like “how dare you sign online!”, I so happy…GO EVAN!! He had confidence to believe  in himself finding the right woman and didn’t settle because he knew what he deserved <3 Women need to feel the same… we deserve love, respect, happiness, but we have to believe it’s out there for us in order to attract / find it!

  3. 3

    The OP has a valid problem, and she asks Evan for his advice.   He responds to her by providing her with said advice (and very good advice, I might add).   I can’t see the connection between advice asked/advice given and failing to understand the average person’s dating experience.   
    Also, I believe this situation is more common than you think.   I’ve often been in this position, and there’s nothing exceptional about me :).  

  4. 4

    Hmmm. In recent times when I’ve suspected or gotten the, “just to let you know, I’m still dating others,” I end it. When a girl really likes a guy, there is no other (and guys should never date a girl that isn’t crazy about them). If after a number of dates you can’t decide between two, neither is likely a great choice. Further, I can’t imagine a man with good market value staying in such a situation, or being comfortable with it after the fact, when he learns of it later.

    1. 4.1

      I know where you are coming from Sal

    2. 4.2

      A guy will if he’s attracted and not wanting a commitment…

  5. 5

    @ SAL9000, that’s your prerogative. You have every right to end it for whatever reason you choose. From a woman’s perspective though, for every guy who ends it because she’s still dating others, there is another (if not more) who will freak out and end it if he hears, after one, two, or three dates, “Just to let you know, there’s nobody else. You’re the only one I’m seeing”. My conclusion? Since I cannot read a man’s mind, cannot know which of the two situations will tick him off, I’m going to do whatever I am comfortable with at the moment.
    Also, who talks about other people they’re dating, on dates? That’s not a date conversation. With most people, it’s don’t ask don’t tell. No one goes into detail about how they’re still dating others, but for the first few weeks, it’s implied that both probably do. If a man I’m dating started telling me about his dates with other women, I’d probably end it too. Not because I think I should be his only one from date one, but because I’d assume he’s playing some sort of a power game with me, and I’m really not into that stuff.
    FTR, I was in this situation two years ago, and Evan’s advice is right on. If you take things slow and stick around long enough, enough facts will come to light to help you decide which of the two (or both) are not good boyfriend material.

  6. 6
    Karl R

    Evan said: (original post)
    “3. Time reveals all.”
    I agree with this, but I also want to add my own warning about this.
    When I got back into dating, I dated two women for 3 months before deciding on one. But to be honest with myself, I could have quickly and decisively made the same choice at any point after the 6 week mark. Was I absolutely sure of my decision beyond a shadow of a doubt? No. Was I sure enough? Yes.
    At a certain point, you’ll be sufficiently sure of your decision. Don’t prolong things after that point.
    Evan said:  (#2)
    “When you carry yourself with confidence, you assume that people will like you and you don’t accept crumbs out of fear you can’t do better, yes, it’s a sweet deal. But it’s a sweet deal that anybody can have.”
    I agree. I couldn’t point at a woman and say with 100% certainty that she was going to date me, but I could be 100% certain that I was going to meet another woman who would.
    Jenna, (#1)
    This isn’t magic. It’s just a matter of acting on self-confidence.
    A month after I started dating my wife, I let her know that I had front-row seats to a U2 concert that was coming up. She was surprised that I could get good seats at an affordable price on short notice. I assured her that I’d paid regular price … because I’d purchased the tickets six months earlier through a special pre-sale.
    My wife: “Who were you dating 6 months ago?”
    Me: “I don’t think I was dating anyone that week, but it seemed a fairly safe bet that I’d be dating someone by the time the show came around.”
    In  three years of buying tickets that way, I went to one show without having a date on the day of the show. (We’d broken up two weeks earlier.)
    SAL9000 said: (#4)
    “When a girl really likes a guy, there is no other (and guys should never date a girl that isn’t crazy about them).”
    Day 1: The woman told me she wasn’t interested in a serious relationship with me.
    One months later: She was still referring to me as her “dance partner” when she introduced me to friends/coworkers, not as her “boyfriend.”
    Three years later: We got married.
    If you’re not boyfriend/girlfriend by three months, it’s probably not going to happen. Earlier than that, it’s a bit precipitous to bail solely for that reason. (Of course, you can choose to bail if you want to.)

    1. 6.1

      Buying tickets for two ! Now that’s an intersting idea to motivate one (particularly men) into getting and organising dates !

  7. 7

    @ Karl #6:
    SAL9000 said: (#4)
    “When a girl really likes a guy, there is no other (and guys should never date a girl that isn’t crazy about them).”
    Day 1: The woman told me she wasn’t interested in a serious relationship with me.
    One months later: She was still referring to me as her “dance partner” when she introduced me to friends/coworkers, not as her “boyfriend.”
    Three years later: We got married.
    If you’re not boyfriend/girlfriend by three months, it’s probably not going to happen. Earlier than that, it’s a bit precipitous to bail solely for that reason. (Of course, you can choose to bail if you want to.)
    There was another thing I wanted to add to this. I personally am not a big believer in instant chemistry (i.e. when the other person is crazy about you early on). They don’t know me yet. I don’t know them. How come they’re so crazy about me? Is it because I’m so awesome or because they think I’m something I’m not, they just like the feeling of being in love, they’ve had a six month dry spell just at the time when I came along, etc? Are they going to be able to sustain this crazy-for-me feeling for the rest of their lives? how about for the rest of this year? As a male friend of mine once told me, “someone who goes from zero to boyfriend in sixty seconds, will go the other way just as quickly”.
    Interesting that you mention concert tickets. This summer I happened to buy tickets to see a band both my bf and I liked, three weeks before he broke up. What can I say? my 18yo son and I really enjoyed that show! I’ve never thought of buying two tickets in advance when you don’t have a second person to take at the moment, but this approach does sound interesting!

  8. 8

    You decide whether someone’s a keeper or not when you realize what kind of person   will show up in a crisis and how will the two of you work together as a team.   This is in addition to whether you have chrmistry, love each other etc.   Sometimes you can be with someone for years and not really know this because the relationship hasn’t really deepened or nothing challenging has happened.   Sometimes you do know in a short period of time because the relationship has been tested.   
    My husband and I have only been together 16.5 months (married after a year) but we have been through a lot more than most couples.   We know how the other will respond with trust, loyalty, and generosity.   So yes we are one of those couples who just knew early on but it was based on a solid foundation beyond chemistry (though there was plenty of that).   The other day I was worried a certain unwanted event might happen and he said don’t worry sweetie we will just handle it on the fly like we do everything else and it will be fine.   Unless you have that kind of trust and confidence in your relationship I wouldn’t recommend getting married.

  9. 9

    @KarlR # 6 “I couldn’t point at a woman and say with 100% certainty that she was going to date me, but I could be 100% certain that I was going to meet another woman who would.”
    Yes, like you I have 100% certainty I can always find a woman who WILL date me but it’s rare I find a woman who WILL that I WANT to date as well. Finding “dates” is easy online. Meeting someone I’m actually interested in pursuing that’s into me as well  is the problem.  I keep at it though. 🙂

    1. 9.1

      Ain’t that the truth? Haha. *high 5*!

  10. 10
    David T

    I was in the situation of dating two women at the same time about a year ago. I didn’t plan it that way; one appeared to not want to play and then I started with the other…and then the first came around. They both had some awesome qualities and all my friends said I was not doing anything wrong but still, 3 weeks into this I felt uncomfortable. That is just me. So I called the one I saw the best chance of a future with and laid it out. I told her I wanted to be exclusive with her because I was not comfortable continuing to date two women. She was not ready for that yet, so I went on to date the other woman. She was fantastic, but my hunch was right; we were not a good fit in the long term and I broke it off after about 2-1/2 lovely months with her. It is up to the individuals own comfort level. There is no magic time.

    JB6 I totally sympathize with you. I have not been able to muster more than a one or two date interest in any woman at all, and the rare few who feel like good matches (one in the last year) have not wanted to play. I don’t believe I am a toxic maximizer. I am not disregarding because of this or that dealbreaker. I usually just don’t feel drawn to them or feel true companionship when I spend time with them. . Many are fabulous and nice women that I would remain friends with if I had the time to keep up with all of them, they just leave me flat. I talked this over with a friend of mine who I did love and date. It is a matter of not feeling alone or lonely when I am with them. A LOT of women have been fun in the moment or on an outing or date, but in the end it has been very rare that I feel understood and not alone when I am with them. So I take breaks from dating, poke my head back out for a half dozen or dozen women, become tired of meeting new folks again and stop for a while. The search continues!

  11. 11

    Such an American problem. In the UK you date one person at a time. Get caought with 2 at any stage and its trouble.

    1. 11.1

      That is how it used to be in the UK  Peter, but unfortunately, now it’s ‘friends with benefits’ or ‘not exclusive’ and polygamous dating for many and I don’t know how they get their heads round it, or manage to escape STDs.


  12. 12

    I was recently in this situation and they both disappeared on me, sometimes they make the decision for you.

  13. 13

    Yea, it’s true. Sometimes, they will make the decision for you…but from my experience, the guys that held out for a little while were worth it. The impatient ones were just looking to score and bolted when it was taking too long.

    If you’re seriously looking for a lifetime partner, take your time. Time does reveal all. I’ve dated multiple guys at one time before. I didn’t feel guilty about it. I have no obligation to any of them. My obligation is to myself to find the right person for me. It’s in your best interests to do so. Let them pressure away. Tell them you move at your own pace and leave it at that. If they really like you, they’ll respect that.

    There will come a point that it will appear you are just stringing them along, though…and men HATE that. Like a previous commenter said, I would say 2-3 months in is the cutoff point. By then, you should know who you like. Honestly, it took me about 4-5 weeks to figure out if I really liked a guy.

    1. 13.1

      Yes. I am not a man but know them well enough to know a lot of them do not like playing games – those who are not players or PUAs anyway. Usually they know straight away if they want to date a woman, and make up their minds pretty quickly about whether or not to continue dating. Men generally don’t want to waste time because time spent with a woman they are not that keen on, or who are not that keen on them, is time that he could have spent more productively with someone else.
      So if a man “pressures” you, it may not be because he only wants one thing, but because he doesn’t want to waste any more time than he has to. Sounds brutal to women, but it’s true.

  14. 14

    Hi everyone, and thank you so much for answering my question, Evan.

    Yes, the situation did resolve itself in the end. I decided to pursue something more serious with Bachelor #2 and we dated for a few months before I came to the realization that we were far too different in terms of the kind of life we want to live, and even more challenging, he is a non-communicator. For these and other reasons, I ended it. In fact I’d gotten some advice from you about the situation when I was briefly part of your Forum.

    I then contacted Bachelor #1 to see if we might meet up again and he was open to it. We went out once but I discovered on the date that the things that turned me off about him previously were still a factor (at age 50, he didn’t have his own place, was living with family members after moving out of a house that he had shared for years with a bunch of guys, among other things) so that relationship also didn’t move forward.

    So ultimately, the “juggling” resolved itself within a month without the physical side of things going too far. Evan, I agree with your advice on all counts. For me, I think the lesson is to try to avoid such situations in the future if possible. As Peter said, if you get caught and haven’t been honest about what you’re doing, it could cause a lot of trouble.

  15. 15

    I would think if it was true love there would be no comparison.

  16. 16

    I am similarly trying to figure out what to do about dating two men. I met them both online, had our first dates within two days of each other, and it’s now two and a half weeks later and I’ve been on 3-4 dates with each. I am very interested in both, and they appear to also be very interested in me. I feel the need to let each know that they are not the only person I’m interested in, though I have no desire to meet any more men. I am also limiting the physical side of things until I have at the very least informed both of them. Thank you all who mentioned timelines–I wasn’t sure how soon I should be expected to figure out what exactly I want and who best fits the bill. Hopefully the next time I see each of them I will be able to figure out how to talk openly and without too much pressure about this.

  17. 17

    I have no idea how old this post is – but my comment is to Evan.

    It is NEVER okay to break up with someone via email if you have been seeing them regularly (even if you weren’t exclusive). We deserve to have that uncomfortable conversation in person, or at the very least a phone call. That’s called manners. And if you are “confident enough to have this job” then you should realize that.

    1. 17.1
      Karmic Equation

      Nope. Men don’t care about “closure”. Women do, but only if a guy she really likes ends it. If she wasn’t crazy about him, she doesn’t care. Be honest about that. It has nothing to do with manners.

      If you’re not exclusive, then ending by email or text is MORE than enough. A fade out after more than 3 dates is not nice, and at least a text is required. But phone call or in-person breakups after only a month of dating (probably 3-5 dates)? Not required at all.

      1. 17.1.1

        I don’t know about that, Karmic. Maybe I spent too many years of my life married, but I’ve never been comfortable juggling multiple girlfriends (or potential girlfriends), even when none of them have (yet) become exclusive. Just doesn’t feel ok, somehow. Your mileage may vary…

        1. Karmic Equation

          I think it depends on the guy.

          I’ve dated both age appropriately and inappropriately, lol.

          And the ones looking for relationships tend to date one at a time.

          However, men who’re not really ready to settle down yet want to date multiply.

          A woman assuming a guy isn’t ready to settle down yet is better than wishful thinking that the guy she’s dating IS ready to settle down…with HER…until she gets more information, which she can only get by having a series of dates with him.

  18. 18

    In my day, this is what was called two timing and wasn’t highly regarded as it leads to the quandary you are in now, and someone always inevitably gets hurt.   Stick to dating one person at a time and if it doesn’t work out finish with them before finding someone else.  

  19. 19

    Does anybody have any consideration for the person who is going to be the one who  is dumped in these situations?   Perhaps it is better not to get into these situations in the first place.


    1. 19.1

      @ Katy #19
      “Perhaps it is better not to get into these situations in the first place.”
      Perhaps it’s better not to date at all; that way there’s no chance of getting hurt.
      Katy, the letter-writer was dating these two men for 2-3 weeks! If somebody is upset about being “dumped”(?!) after such a short time then they might need to learn how to cultivate justified expectation in dating.
      Perhaps they should consult a dating coach, or read a blog. Hmm…

    2. 19.2
      Karmic Equation

      It depends on what one means by “dating”. If neither guy has stepped up to be her boyfriend, then she has the right to date either, both, or someone else until she finds her boyfriend.

      If she’s inclined to have sex with both men and neither man has asked her to be his girlfriend. She’s not two-timing and can (and should) continue to date them both and others if she wants to, until SOMEONE steps up to be her boyfriend…and she agrees 🙂

      In these scenarios, with dating meaning going out but no agreement of commitment in terms of being bf/gf, if one of the guys gets hurt, it’s his fault for not stepping up sooner. Timing is everything.

      If both men happen to step up at the same time, well, again, timing is everything. If one or the other asked her to be his gf before the other, that guy wouldn’t get hurt.

      The OP’s quandary is that she’s uncomfortable having foreplay with both guys. Well, imo, she needs to get comfortable until one of them steps up. If both press for sex, she gives both of them the EMK speech about “sex only in committed relationships.”

      There’s no quandary if she gets comfortable with foreplay with both guys and doesn’t have sex with either until one offers commitment. Murply’s Law says if she chooses before any offer is made, the one she chooses will probably be the wrong choice and not step up after all and then she’s lost the other one. Murply’s Laws suck.

      Ladies, if you are lucky enough to be dating two men whom you like, let yourself enjoy foreplay with both until someone steps up to be your bf. If neither do once you give your spiel, move on. If both, then you make a choice. If only one does, give a nice dear john speech to the one who didn’t want to commit.

      This is a good problem to have.

      1. 19.2.1

        I disagree. I think you should date one person at a time. Otherwise dating multiple people simultaneously forces people to commit too quickly because they don’t want to lose that person to another person.

        If I was taking my time getting to know a girl (one or two dates a week) and she was casually sleeping around because we weren’t ‘official’ yet I would drop her.



        1. Karmic Equation

          This is assuming that the man in this scenario is only dating one woman at a time.

          That is NOT a good assumption on many women’s parts (and, unfortunately, MOST women DO make this assumption, which is why many are left distraught when the man disappears, most likely after choosing one of the other women he was dating).

          It’s much wiser for BOTH genders to date multiple people until the guy asks for exclusivity.

          Asking women to date only you, while YOU are dating others, is the height of hypocrisy.

          And again, if you ARE dating only her, why don’t you tell her that’s how you operate? Assuming that is the truth and you’re not speaking in technicalities.

  20. 20

    Call me old fashioned, and call it dating, seeing someone, whatever, even if there is no sex involved – emotions are, it is not all about sex, but getting involved with two or more people at once, getting yourself and they confused, this going on for weeks, even if they all know about each other, is not fair and the person doing this is the one who perhaps needs the counselling.   Just what is wrong with dating one person you are attracted to, giving it time to see how it develops and if it doesn’t then end it and date someone else.   People are not items to be tried and trialled  simultaneously and there is such a thing as respect, or at least there used to be.

    1. 20.1

      You must be twelve years old.   Going out to get lunch with one girl and then going to the movies in a couple days after with another isn’t getting involved emotionally with two women… You seem to be one of those people who are very jealous and possessive and you seem to have a jaded view on relationships maybe even life.

      If you are just dating one at a time and letting the other slip by in the way side how are you not missing all those opportunities? I am seeing two wonderful women right now and it just happened to work out that i started seeing them at the same time.   Never happened to me before but i owe no one an explanation as i have no idea I am even the only person they are seeing.

      I think everyone should just live life and do what makes them happy.   If you find someone who is into you and wants to take the ride with you, let them.   I would never turn anyone away unless i was MARRIED and had an obligation to.

      I really do wish you luck though… and hope you open up you view on relationships and life.   these things arn’t separate case files… In the end i recommend everyone to do what makes them happy.   Not what some stranger on the internet deems moral…   You could be an axe murderer… 😉

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