How to choose between two amazing people?
February 2, 2009 1:29 PM   Subscribe

Relationships: How do you choose between two perfectly amazing people?

Some context: I am not a "sport-dater". Especially as I've gotten older, I am more relationship-minded, hoping for longer-term, substantial partners that could someday lead to marriage. I've had an appropriate number of girlfriends for my age, but am not a womanizer or looking to add notches to my belt. That said, I've made some life changes in the past year (the most notable being losing a significant amount of weight) that seems to have had a positive impact on my social/dating life. And so I've found myself with a particular predicament that I am unfamiliar with handling:

About 7 weeks ago, I met someone via an online personal ad. There were no expectations from either side going into it, but she turned out to be fabulous. There is almost literally nothing wrong with her, and she seems enamored of me in return (which is nice). We had a great rapport early on, she has a good sense of humor, is grounded, sweet, thoughtful, intelligent, mature, an open communicator, is very beautiful, and we are sexually compatible. Although we don't have an incredible amount of things in common (which is always understandable from my perspective), we seem to share many long-term goals, and are looking forward to seeing the relationship develop into something formal. When we first met, we both were up-front about the fact that we are dating people, and that since we had just met, the implication was that we were not exclusive. But over the last month or so, it's becoming obvious that we are headed towards a more formal boyfriend/girlfriend relationship. We've been introduced to several of each other's friends, but have not met any family yet. Neither of us are sleeping with anyone else, and she's told me she hasn't been looking for any new dates, but it is still ambiguous (out of respect for her privacy) whether she cut off her dating with anyone else she was already seeing at some point in the last 7 weeks. I definitely get the feeling I am the only one she's seeing, if for no other reason we spend enough time together that it would be almost impossible for her to be seeing anyone else. We've made tentative plans to spend a week together on vacation in March, during which time we would begin to meet each other's families. This relationship is off to a perfect start.

And then... I happened to meet someone else.

Quite honestly I was not looking, being more than content in the blossoming relationship with Person #1.

Person #2, who I met about 4 weeks ago, is also amazing. Someone I would describe as "my type", even though I didn't think I had one. She's also very intelligent, creative, fun, passionate, severely attractive, and also seems to be very interested in me (which is quite flattering). We both felt an immediate and strong connection to each other, and have a great pseudo-feisty banter/rapport. We've gone out socially in groups a couple of times (and ended the evening alone with each other) and while there have been some physical "interactions", we have not slept together. Last night I told her that I wanted to let her know that while I am single, I have been dating, and dating one person in particular for about 7 weeks. She said her stomach dropped at that news, but seems confident that we have a great connection, and I cannot deny that. She then told me that she definitely sees the potential for this to become a relationship if I were interested. There is, however, a not-insignificant factor to consider with Person #2: We work together. And have, by definition, a fairly close working relationship. Technically I am also in a "supervisory" role in my office and she is not, and while we are more like peers and working partners to one another, there is technically a title difference that my office might find troubling when (not if) they find out that we are dating. We have both agreed that we are at a point in our lives where a relationship is more important to us than "office rules" or adhering to the common wisdom of not dating someone you work with, and that we are mature enough to deal with the work situation, even if things didn't work out romantically. While working together may be a red flag for some people, I consider it a good thing: I've always wanted to date someone within my industry, to share that common bond, and am very excited about that prospect.

So... I don't know what to do. If either one of these people existed without the other, I would be completely thrilled and could definitely see a happy, healthy long-term relationship with either one. But I feel, because I have historically been a serial monogamist, a bit out of my element being in this position. It has never happened to me before and I don't know how to move forward.

I think my next step is finding some way of telling Person #1 about Person #2, but I'm not sure to what end or how to broach the subject in the most tactful way to minimize the surprise (and potentially insult). I'm sure she will be very disappointed to hear about it, and I can't imagine the reaction will be good in any way. Alternatively, I could decide to stay with Person #1, and tell Person #2 that I've made that decision.

I also know that sooner than later I will inevitably have to choose between the two, and that gets back to the crux of my question: I don't know how to do that. They are both, at least at this early stage in the respective relationships, perfect. I have NO complaints or significant "concerns" about either of them, and I simply cannot fathom choosing one over the other, because I wouldn't be able to tell the other person why: neither has done anything even remotely "wrong" so far in the courting process, and the potential is strong for a long-term relationship with either one. I also don't even know how to go about deciding who to "choose". Do I make a Pro/Con list? Go with gut instinct? (even that sounds impossible) Flip a coin? Pick the one who is marginally (at best) more attractive? Financially successful? Try to guess who would be a better fit in a long-term relationship? (either one would seem fantastic.) They both give me butterflies.

I know: this is a "good" problem to have in the grand scheme of things, but I'm starting to feel sick even thinking about it, knowing that either Person #1 or #2 is going to be potentially heartbroken and I am going to lose one of them... and for seemingly no good reason at all. I recognize that either way, a decision must be made sooner than later to minimize heartache for everyone involved.
posted by anonymous to Human Relations (22 answers total) 4 users marked this as a favorite
if you ever find yourself trying to decide between two people you aren't ready for either of them.
posted by nadawi at 1:40 PM on February 2, 2009 [28 favorites]

posted by Jaltcoh at 1:42 PM on February 2, 2009

You've already started a relationship with #1 that you have planned to carry into the future. But now you like #2 as well. Seems to me that logistically, at least, it would be easier to tell #2 that things are getting too serious with #1 to carry forward with her. Then try to have a good work relationship with #2 while things progress with #1. If #1 doesn't work out, it's possible #2 will still be available. OTOH, if you go with #2 now and try to go back to #1 later, she'd be legitimately mad about having been thrown over for some hussy you work with.

But in matters of the heart, logistics don't win the day. If you thought you were happy with #1, but were still looking, enough such that #2 drew this much of your attention, maybe #1 is not the girl for you. But if that's the case, maybe #2 isn't, either, because you don't seem to like her any better. And since you work with #2, she might be a constant temptation if you try to take things forward with #1.
posted by rikschell at 1:44 PM on February 2, 2009 [2 favorites]

This isn't a "good" problem to have. Neither one of them stands out enough to you to make this decision easy, but you feel like you've got to make a choice because... you have to be with somebody? I would just keep dating around until you're sure. This is clearly not the right time to make that choice.
posted by katillathehun at 1:46 PM on February 2, 2009

What's with all the exposition?

If you're trying to think your way through this I can guarantee you that you're on the wrong path.
posted by tkolar at 1:47 PM on February 2, 2009 [2 favorites]

also, if you tell #1 about #2 and then choose #1, she will never trust your "i'm working late" line.
posted by nadawi at 1:47 PM on February 2, 2009 [1 favorite]

You've known these two people for such a short time, how can you really say they are amazing and equally perfect? For starters you risk measuring them by very superficial standards.

It's not like you've known these women for years and you have to decide TODAY who you're going to marry.

Further, you're making this out like you're the only person in the relationship. Did it ever occur to you that one or both of these women may decide that they don't want to date you?

I question the either-or premise. What's stopping you from dating them both? As long as you're straight up with them that you don't want to date exclusively, and you don't lead them on, you can draw both relationships out a bit longer to get a better feel for their long-term potential.

Further, you've already got more time in one than the other. I'd trend toward the one you've been with longer, and then if things don't work out, you might be able to pickup where you left off with the new girl.
posted by wfrgms at 1:51 PM on February 2, 2009

You spent a whole lot of verbiage justifying why the work relationship will not be a problem, enough that it probably will be a problem.
posted by benzenedream at 1:51 PM on February 2, 2009 [3 favorites]

I'm starting to feel sick even thinking about it, knowing that either Person #1 or #2 is going to be potentially heartbroken and I am going to lose one of them...

Or you could lose both. That's life. You need to start being really honest here- you need to decide what you want to do, and then you need to tell #1 tonight about what's going on. It seems that you've led her to believe you weren't dating anyone else. That probably wasn't very nice. Will she still want to date you after she finds out, even if you "choose" her? Maybe, maybe not. Maybe it wouldn't work out with her even if you never told her about this whole business.
posted by ThePinkSuperhero at 1:52 PM on February 2, 2009 [1 favorite]

and then you need to tell #1 tonight about what's going on

Whoa whoa, I don't think you need to do that right away. If you do choose #1 then tell her later on, when the stuff from the beginning of the relationship won't matter.

If you didn't talk to or see both of them for a week or two, who would you want to see more? Who would you be more excited to tell about how you've been and to find out what's been going on in their life?

Since you've already slept with #1, and since most relationships don't work out and there's a bigger chance of awkwardness in the end if you continue seeing #2 and then break up, I'd just stick with #1. But only if you know you won't be tempted by #2. And if you think you'll be tempted by #2 then maybe you shouldn't commit to either one yet.

Also, since #2 already knows about the existence of #1, and it sounds like she was hurt by it, I think it would be best if you don't lead her on - make your decision now to either be with #2 or not, so she doesn't sit around wondering.
posted by KateHasQuestions at 2:03 PM on February 2, 2009

We have both agreed that we are at a point in our lives where a relationship is more important to us than "office rules" or adhering to the common wisdom of not dating someone you work with, and that we are mature enough to deal with the work situation, even if things didn't work out romantically.


I'm sorry, but this is ridiculously funny. Mature? Really? Did you see what you just wrote? You are neither mature nor smart enough to shit where you eat and to compromise your current job by sleeping with a subordinate. You might be able to justify to yourself the "breaking of the rules" but you're not going to be able to convince H.R.

And that's the problem with your whole question. You're trying to find justification for your behavior. You are developing a relationship with #1 but you don't want it. If you did, you would have done so by now. You like to view yourself as being exclusive in action but not in name because you don't want to settle down with #1. If you did, #2 wouldn't exist. So why keep playing games with #1? If what you say is right (and considering your self-worship, I can't take much of what you say seriously), then #1 wants you and you don't want #1. In fact, you want to keep dating around and finding the next girl who interests you and causes you to "feel a spark" or however you label it.

To you, #1 is the choice you feel you "should" do while #2 is the exciting passionate one - the one that breaks the rules and seems dangerous. You are not at the point in your life where you can provide #1 with a relationship so tell her that you're interested in someone else, that you've been seeing someone at work, and that you'd rather jump at the next fish to cross your path.
posted by Stynxno at 2:19 PM on February 2, 2009 [5 favorites]

Neither of us are sleeping with anyone else, and she's told me she hasn't been looking for any new dates, but it is still ambiguous (out of respect for her privacy) whether she cut off her dating with anyone else she was already seeing at some point in the last 7 weeks.

I suspect that you're fooling yourself so that you don't feel as guilty dating around. "I'm not looking for any new dates" is pretty solid code for "I'm only seeing you."

You're planning vacations with this woman. My gut instinct is that your everything-but-sex interactions with this lady from work are inappropriate in light of your relationship with #1. I also suspect that you're thinking with your little head, not the big one. The situation with #2 at work sounds like a disaster and you've overtalked enough about why it's not for me to guess that you know what a mess you're getting yourself into.
posted by PhoBWanKenobi at 2:20 PM on February 2, 2009

While I agree with what's been said here as far as you not being totally honest with #1, I decidedly DO NOT agree that just because you've had the misfortune of meeting two great people at the same time means you're "not ready" to settle down or not mature enough to deal with any of it.

I understand the paralyzing doubt, the worry that you're going to make the wrong choice, but I've come to believe the if you let this kind of indecision hinder relationships, you'll always be unhappy.

My advice is to pursue the #1 relationship, and wait on #2. I think it's true that #2 sounds more like short-lived excitement that could possibly (would probably) end in disaster (both personal and professional). Eventually you need to be honest with #1, but whether you do so now or later is up to you. It really depends on her temperament.

Most importantly, try not to let regret tinge your relationship, whichever girl you choose.
posted by Isingthebodyelectric at 2:37 PM on February 2, 2009

Here's a hypothesis: Your new ability to attract women has made you reluctant to commit to one person when a better one might come along at any time (rather than just grateful to have an OK candidate available at all). Person B just happened to be in the right place at the right time to play the greener-grass role.

If this is true, and you go with person B, then before long you will meet person C and be all like "Guys, I don't know what to do, she's beautiful perfect etc. and unlike person B she's not in my industry, so we can learn more from each other instead of rehashing shop talk!" This cycle will repeat until you either move past it or die alone.

On the other hand, person C might also come along if you ditch person B for person A. Really the only way to stop person C coming along is to change your mindset so that you are no longer vulnerable to that trap. That's something you do on your own, independent of who you are dating.

So I am sort of with the folks who say that you aren't ready for either of them, although I don't mean that in a harsh, "You don't deserve a woman!" way. More in a "How your next relationship plays out might be less dependent than you think on exactly who the partner is" way.
posted by No-sword at 2:43 PM on February 2, 2009 [3 favorites]

We work together

Such a bad, bad, bad idea.
posted by turgid dahlia at 2:55 PM on February 2, 2009

Tell #1 sooner than later, because in part her reaction will temper the rest of your relationship with her, even if you end up just being friends. Maybe bring up your own uncertainty of #1 dating other people now, and then mention #2 but your decision to "be true" to #1.

Agreeing with No-sword - this is not really a "good problem to have in the grand scheme of things," but something you are enjoying now, because the old you never thought this was possible. I know something of that - when I finally started dating, I had a study partner find me more appealing than I realized, and was a bit giddy at the situation. I had been dating my girlfriend of the time for a while, so there was no debate for me.

Work relationships can survive, but the number of "what ifs" that can make things go wrong are much higher when dating someone who is in your office environment. I understand having someone share the interest in your field, but having someone share your work environment is much different, possibly resulting in burn-out over being near someone all the time.
posted by filthy light thief at 3:35 PM on February 2, 2009

It sounds like you're going to regret either decision that you go with (in the mourning of a lost opportunity sense), so why not stick with #1 and not have to also regret messing up your work situation and hurting the feelings of a "perfect" girl who probably thinks you're exclusive?

If the balance is so precise, something little like that should easily tip the scales.
posted by Pomo at 6:31 PM on February 2, 2009

How can you even think of having a long term relationship with someone who has next to nothing in common with you? What are you going to have to talk about when you both grow up and realize that looks fade and the butterflies die down?

Pick the one who is marginally (at best) more attractive? Financially successful?

Pick the one who's the most superficial, conventional, and shallow so she won't mind as much when she realizes what your real values are. Seriously. The way you talk about it, you might as well pick the one that matches your furniture.
posted by aquafortis at 6:46 PM on February 2, 2009 [2 favorites]

As others have said many times in the past, "Don't piss where you swim" or other variations on don't date coworkers. Yes, coworker dating can succeed. I've seen it. It's rare, but it can happen. Far more commonly it doesn't work out. Sometimes that can be a quiet thing for all involved, and no big problem. But I've also seen it turn into raging thermonuclear fireballs of hate, loathing and odious disgust that bystanders didn't even want to be on the same floor of the building when the two former lovebirds were in close proximity, and it always ended up with someone taking the long walk, sometimes the underling who had no political capital, sometimes the supervisor who "should have known better". Something to factor in to your contemplations on dating door #2.
posted by barc0001 at 2:06 AM on February 3, 2009

The thing that JUMPED out at me from your post is that you aren't interested in either woman. You talk about their wonderful characteristics like you are listing the personality traits of a fictional character. You talk about their feelings but nothing of your own. I cannot find even one instance where you say "I feel x way about girl A or B."

Girl A is "enamored" with you, which you think is "nice." Girl B is "very interested" in you, which you think is "quite flattering." It seems to me that you have two girls interested in you, which is a new thing for you, and you don't want to let either go. You are so wowed with the new sensation of having women want you that you don't care and/or are not thinking about how YOU feel about THEM.

Do you love either of them? Do you even like them? Are you crazy about them? Do you think about them when they aren't there? Do you feel giddy, happy, content, ecstatic, light-headed, etc? It's like someone described these two women to you (open communicator, attractive, etc) in order to set you up on blind dates. Now that you've met, how do you actually FEEL about them?

It seems like you still have some more "life changes" to make. Dump them both (ie, stop stringing both of them along).
posted by thebazilist at 9:27 AM on February 3, 2009 [5 favorites]

Ignoring all the judgmentalism & amateur psychology in this thread, I'm going to address the crux of the question: "How to decide between the two?"

Flip a coin. Assign, say, heads = #1 & tails = #2. If your first reaction upon seeing the result is disappointment or elation, you'll know which way your subconscious has already decided*.

* amateur psychology alert!
posted by UbuRoivas at 6:53 PM on February 3, 2009

For another kind of analysis, you might like to evaluate each of these prospective partners in terms of StickyCarpet's five-legged table model.
posted by UbuRoivas at 7:06 PM on February 3, 2009

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