Should I try to date him or is it already too messy?
April 21, 2009 8:47 PM   Subscribe

Should I try to date him or is it already too messy?

I've recently learned that a casual friend (Person A) is attracted to me. While I don't feel the same way (I feel neutral about it), I'm not averse to a couple dates to see if my interest is piqued.

However . . . I have a bit of a history with one of his friends (Person B). This is not something anyone knows. This friend is in a relationship and even if he wasn't, I'd be unlikely to pursue something. But I am maddeningly attracted to him and have enabled him in a few instances of infidelity. I'm not trying to explain or condone my decisions, it is what it is.

Person A, from what I know of him, is funny and intelligent and sometimes kind of an ass. Whether he is the kind of an ass I can accept in a relationship (dating or more significant) has yet to be decided. I guess the only way to find out is to date him. I'm not terrifically carnally attracted to him (unlike my feelings for Person B who I'd spend a week in bed with), but that often changes when I get to know someone.

But I'm hesitant. I'm a bit blase about fidelity (I try to remain faithful, but don't beat myself up if I slip as I have a couple times) and to be honest, I'm not sure that I wouldn't slip with Person B. If I started dating Person A, I don't know that Person B would see that as a boundary, frankly. The possibility of our hooking-up would likely be the same as with me being single. Or maybe not because there's a friend involved (bros before hos?)

I guess I'm worried about my track record and Person B's track record and how it could affect Person A if (hypothetically) the dates lead to something significant. Like I said, I'm neutral about Person A, but I'd like to give him a chance since I like him as a person and he's put himself out there, which I think is commendable and scary.

But is there already too much to navigate? I mean, I'm never certain that I have the capacity to be faithful, but I usually don't let that stop me from dating. I go with it, try to be good, deal with consequences if I have to (it's happened far less than I make it sound, but it has happened). But A and B are friends.

My indiscretions with B have been infrequent, but there was a recent makeout, the day before A asked me out. If it hadn't been for that, I would have accepted a date, no questions asked.

Does the potential bad outweigh the potential good of dating person A? Or should I just go for it?

(We're all in our late 20s/early 30s. I'd rather not have lectures about the wrongness of hooking up with someone in a relationship. There's a throwaway for those who want it).
posted by anonymous to Human Relations (25 answers total) 1 user marked this as a favorite
as an outsider, it seems like it would get too messy unless A is only attracted to you at a legitimate casual level- which, of course, we do not know.
posted by the aloha at 8:52 PM on April 21, 2009

Yes, it's too messy and you know it. Putting my own feelings about fidelity/infidelity aside for the moment, everyone is going to feel fucked over if one of you is not faithful. In strictly practical terms, the payoff is less than the risk anyway you slice it: a few so-so dates versus pissing friends off indefinitely. Go meet some people where the risk/reward ratio is better.

Returning to my own feelings about infidelity: Be honest and set people's expectations upfront. The problem with infidelity isn't the sex, it's the lying. You already know it's a shitty way to treat people, as evidenced by your post. Why spend time with anyone you don't respect enough to be honest with? There's nothing wrong with doing something other than monogamy, but that's not a situation of such a different category that you can't respect other people.
posted by Inspector.Gadget at 8:57 PM on April 21, 2009

Setting aside all the fidelity / infidelity stuff, you just don't seem very excited about Person A. Life's too short.
posted by salvia at 8:57 PM on April 21, 2009 [3 favorites]

So you're suggesting that you may not date Person A for fear of hypothetical drama hurting Person A (and not so much you or anyone else)? Seems like you're unfairly protecting Person A from risks he's not even aware exist. His view of the emotional risk/reward in this situation may be entirely different from your assessment.

Besides, he has already taken the emotional risk of putting himself out there, so maybe he's less risk-averse than you think.

I'd say give the guy a shot.
posted by mullacc at 9:26 PM on April 21, 2009

You really don't seem excited about A ... maybe that's because he's available ... it seems like you're more attracted to the thing you can't have. Or it might just be because you're a better fit with B. In any case, you should pursue a relationship with someone you actually want to be with, not with someone you're settling with because it's all you can get at the moment.

As far as your prior involvement with B ... morality aside, it bodes ill for your ability to be monogamous if you decide to date A. And if you sleep with B while you're dating A and he finds out, you've probably ruined a friendship. Don't be that person.
posted by Happydaz at 9:28 PM on April 21, 2009

I guess you have to decide, are you dating Person A as a potential lifepartner? If so, you've already admitted to thinking he's an ass, finding him sexually non-interesting, etc. That's not a very good way to start a relationship that you're thinking might be long-term, unless you have things which pull you together outside of the dating thing (do you both paint? do theater? like medieval french poetry?).

If you're looking to get a few kicks and have someone to do things with, you'd have to make sure your involvement with A isn't leading him on. If HE is in this for the long-term, but you aren't, it will be unpleasant when you have had your fun and he's not ready to let go.

I have no monogamy qualms, so I say, date 'em both, have sex with 'em both, and even all together if they're into it. But that's just me. YMMV.
posted by hippybear at 9:28 PM on April 21, 2009 [1 favorite]

There's a famous philosophy argument (from a philosopher named Michael Smith, though I believe he borrowed the facts from someone else) that goes something like this: the right thing to do just can't always be what a person with good character to do. Suppose I'm a squash player with a really bad temper. I think that a person with a good temper (a virtuous person) would, after losing a squash game, go up to the net and shake his opponent's hand. But I'm a person of bad character, and I know that if I go up to the net, I'm likely to lose my shit and hit my opponent. Therefore, I ought not to go up to the net.

This is, to be quite blunt, your situation.

You ask for no lectures about fidelity, but the infidelity issues are precisely what makes this so messy -- it's impossible to separate the fuckedupness of the cheating from the reason the dating shouldn't happen. You're considering this guy and *planning* to "slip" -- and wondering whether or not it's too messy. Yeah, it's too messy for just that reason. Seriously. Why put yourself in a situation where you're going to act like an asshole to someone?

And so because you have a bad character for cheating, you should not do what someone who has a good character for cheating would do.
posted by paultopia at 9:35 PM on April 21, 2009 [15 favorites]

If you're making a list of reasons why you can't be with Person A, then don't date him.

I don't want to assume but your question reminds me of a conversation I have with a lot of my single straight female friends - just because someone is attracted to you does not make you morally obligated to date him. Or fellate him. If you hear he's an "ass" and are already planning on cheating on him? Sounds like a self-fulfilling prophecy.

Likewise, with Person B, you say you are prone to 'slipping' which to me says either a) you love the drama that cheating brings or b) you should look into an open relationship/polyamory/other non-monogamy. Maybe Person A would love to have a FWB setup with you. Maybe they both would. Mullacc is right - you are protecting this Person A from things that he might not have a problem, say, a casual open relationship.

If you decide not to date Person A, tell him your social circle is already too incestuous and leave it at that.
posted by SassHat at 9:36 PM on April 21, 2009

("what a person with good character to do" should obviously be read as "what a person with good character would do")
posted by paultopia at 9:37 PM on April 21, 2009 [1 favorite]

Skip over getting involved with Person A. You seem to only have so-so feelings for him anyway. In any event, he may be aware of your relationship with Person B already, since they are friends.

Even if you don't get involved with A right now, there is always a possibility of a relationship with him happening in the future, and perhaps at a time that you are more receptive.

What's the deal with B, though? You seem very hung up on him. If you are totally crazy over him, and he is staying in this relationship with another person, he is getting ALL the good stuff and you aren't getting any of it. I wouldn't base your relationships on how things are going with B anymore. You'll just make yourself miserable.

Regardless of your decision, good luck - and do let us all know how it turns out!
posted by junipero at 9:43 PM on April 21, 2009 [1 favorite]

Don't bother.
posted by turgid dahlia at 9:56 PM on April 21, 2009 [1 favorite]

I find the whole "bros before hos" thing incomprehensible, but that said, I don't see how A's friendship with B is an issue here.

Even if they were perfect strangers, the crucial facts would be:
  1. You've got the hots for B.
  2. A doesn't do it for you — in fact, so much so that...
  3.'d cheat on A with B given half a chance.
Friendships or no friendships, that's a pretty straightforward situation, and not really a ringing endorsement for A.

Don't settle. It's not worth it, and it's not fair to the guy you're settling for. Wait until you meet someone so awesome that he blows B out of the water — or, for that matter, until you and B get over your respective hangups and decide to give it a shot.
posted by nebulawindphone at 9:59 PM on April 21, 2009

"I'm a bit blase about fidelity"
If this statement is general to your dating life, you should be entering polyamorous/open relationships, not monogamous ones. The people I know in open/poly relationships sometimes have trouble balancing partners, especially if there are several primary partners, but at least they're being honest about it. You can have your poly cake and eat it too without being an asshole to some undeserving partner.
posted by Derive the Hamiltonian of... at 11:10 PM on April 21, 2009 [3 favorites]

is it really fair for you to be dating anybody while you are hovering in the "I'll sleep with B at the drop of a hat" pattern?
posted by 5_13_23_42_69_666 at 11:16 PM on April 21, 2009 [1 favorite]

I think you're asking the question backwards. You're really not into Person A, but you'd be willing to give him a shot because you realize it's very possible you might change your mind. This is a good attitude to have, assuming you don't end up stringing Person A along.

Of course, when Person B sees that you're going out with his friend, he'll probably be much less inclined to continue this torrid affair of whatever sort you guys are currently having, because hey, now you're his friend's girlfriend!

I wouldn't be too worried about Person A. If he's an adult, he can deal with rejection. But if you want to keep fucking Person B (and you seem so sure that both parties want it to happen again, there doesn't seem to be any point to arguing whether it's right or wrong) then it's probably a good idea not to date his friend, because man, then Person B would totally be enabling you to cheat on his friend!
posted by hamsterdam at 11:40 PM on April 21, 2009

The drama potential for this one is very high. What happens when Person A finds out about your indiscretions with Person B and tells B's partner? There's just too much overlap here.

Is Person A into monogamy? Because of it is, dating him while being all whatever about fidelity (with the extremely high potential to be cheating with one of his friends, no less) is a dick move. Don't do that.
posted by crankylex at 6:06 AM on April 22, 2009

Go for it. Life's too short. "A" may surprise you once you get to know him.
posted by torquemaniac at 6:28 AM on April 22, 2009

You should find a Person C.
posted by Brandon Blatcher at 6:35 AM on April 22, 2009 [4 favorites]

Bleh, you couldn't sound less interested in Person A if you tried. It's nice of you to give him a shot, but there are so many others you could give a shot to who aren't enmeshed in this relationship you have with Person B. Go find them.
posted by agentwills at 6:48 AM on April 22, 2009

Do A a favor and don't date him. If I was A and caught you with friend B I would more than likely beat B up and dump you. So save everyone emotional and physical pain and find a C and don't cheat on him.
posted by Mastercheddaar at 7:35 AM on April 22, 2009

What exactly would the point be in pursuing things with someone you aren't interested in, who you are fairly confident you'd probably cheat on? This seems like a good way to earn some bad karma.
posted by chunking express at 8:46 AM on April 22, 2009

"If I started dating Person A, I don't know that Person B would see that as a boundary, frankly"

Why is this a function of Person B's boundaries? What are your boundaries? If they are fluid, then be upfront with Person A that you don't want to be exclusive.

I wonder: do you plan to date Person A to make Person B jealous? Do you have feelings for Person B outside of sex?

There is always drama to be had.... but it comes at the expense of lots of other important things.
posted by cranberrymonger at 9:34 AM on April 22, 2009

You're not even dating A yet, and there's already drama dripping from every sentence of this post. I would do A a favor and leave him out of it.
posted by The Light Fantastic at 11:01 AM on April 22, 2009

paultopia and The Light Fantastic have it.
posted by notned at 11:32 AM on April 22, 2009

Dating someone you ALREADY KNOW you aren't interested in, just to "give him a chance" because he likes you first? This is hell to do. I've done this so many times and I do not recommend it. Not once did I change my mind when I gave the dude a chance. You already know you don't like him. What on earth could he do to change your mind on this? Pull rabbits or money out of his ass? He's probably not going to be a drastically different personality in a dating context- the only real difference is feeling obligated to kiss him at the end of the night.

If you date him, he is going to assume you like him back, and end up getting his feelings hurt. And that's even BEFORE this Person B(oink) drama.

As for Person B...uh, that's also some drama you need to get out of.

I vote with Person C. Or celibacy.
posted by jenfullmoon at 4:10 PM on April 22, 2009

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