As a gay woman, when is it okay to pursue a straight woman?
November 20, 2011 7:27 AM   Subscribe

I am a gay female in my late 20s who has understood my own sexuality for as long as I can remember and has been out to all of my friends for many years. My orientation is certainly not anything I would consider a defining characteristic about myself. The kind of profession I am in, the kind of experiences I have had and my life goals have greatly shaped who I am as a person, and have absolutely nothing to do with who I am attracted to.

For this and many other reasons, even in New York, finding someone who holds my interest past the second or third date has been challenging. Oddly, coincidentally, whatever-ally, I have fallen in like/love with some amazing women over the years. The problem? Minus one who was not all right for me, all of them are straight. My most recent case is a friend from the City who moved back home to Europe. We talk online daily and I recently had the chance to visit. Even if nothing were to ever materialize with her, it still got me thinking.

Gay rights have evolved considerably in the Western world in the past decade. I think this has been a large contributor to it becoming a mainstream idea to view a relationship – gay or straight – as just that, a relationship. Combined with an already semi-iconic idea of women finding their true love in a woman later in life (a perfect example is Bette and Tina from ‘The L Word’), I have begun to question my attractions to straight women.

My question is this: when is okay, or is every okay for a gay woman to pursue a woman who is straight? For those ‘straight’ women who are now with a woman or were ever with a woman, how were you approached? For those gay women now with (or were with) ‘straight’ women, how did you know when it was time to make a move, assuming you were the one who did make the move?

I by no means wish to imply I want to become a predatory person who only views their friends as potential hook ups. I am asking about true feelings beyond simple infatuation.
I understand women interact with other women differently than they do with men, but knowing the other woman may be interested sexually can change the level of comfort and intimacy for the worse. But as I get older, as I continue to fall for women whom society once said were off limits, I am more and more curious to know if and how this is changing. Maybe I have met my soul mate, but she doesn’t know it and neither do I!

posted by anonymous to Human Relations (42 answers total) 1 user marked this as a favorite
My Kinsey score puts me firmly on the (female) hetero side of things, and is no more of a choice I can modify than someone on the opposite end of the scale. My reaction (and I've been approached by some incredibly attractive, strong, admirable women) would be, to be enormously flattered, and then turn you down and hope it wouldn't affect our friendship, if there was one, or one was in the works (the same reaction I would have to a man I wasn't interested in dating).
posted by availablelight at 7:33 AM on November 20, 2011 [3 favorites]

My question is this: when is okay, or is every okay for a gay woman to pursue a woman who is straight?

Sure it is. You take the same risks you would if you were straight and interested in a friend; by approaching the idea that you have feelings for them, you risk them becoming uncomfortable being around you and losing the friendship. Those changes in comfort and intimacy happen in straight friendships that are changed by the introduction of romantic feelings.

There's nothing predatory about having feelings for a friend and asking them if they reciprocate. I've had gay male friends do this (not making a move, but approaching it verbally) and it was more than okay, even though I wasn't interested. We're still friends today and I appreciate their honesty.
posted by Rodrigo Lamaitre at 7:34 AM on November 20, 2011 [10 favorites]

As a straight woman, this makes me uncomfortable. I have been hit on by gay women, and it makes me feel the same as getting hit on by men I'm not interested in (slightly uncomfortable and hoping the attention diminishes so I can have a comfortable relationship with the person). I'm perfectly happy to be friends, and the furthest any of my gay friends has gone with me is discussing my feelings towards women and how I view them sexually (perhaps she was feeling me out?). Having a gay friend hit on me once, get rebuffed, and not bring it up again would, I think, be okay. Provided I felt the boundaries were clear. If I were questioning my sexuality, however, and interested in the particular woman who approached me, this could give me an opportunity to explore.
posted by DoubleLune at 7:38 AM on November 20, 2011 [6 favorites]

How would you feel if your straight male friends, knowing you are gay, pursued you? Wouldn't it make you feel uncomfortable? Especially if it was aggressive, sustained pursuit -- so taking an indication from that, at most make one move (have one chat, etc.... however you want to do it) and leave the ball in their court.

Also, have you considered that you are attracted to these women because they are off limits, and not because they have other magical qualities that no other women have? I'm concerned that you think you're "falling in like/love" and that these are "true feelings beyond simple infatuation" with friends with whom you have never had a sexual or romantic relationship. From where I'm sitting, that's textbook infatuation.
posted by J. Wilson at 7:43 AM on November 20, 2011 [31 favorites]

IMO you might have sex with some of them if you pursued them, but it's not that likely that a relationship would work out if they weren't drawn to this.

There's no moral problem with pursuing if they're not in a relationship...pursue away, some of them might be open to it...but you might be letting yourself in for hurt if it doesn't go anywhere.
posted by Not Supplied at 7:52 AM on November 20, 2011 [2 favorites]

Middle-aged mostly-lesbian bi chick here, here.

Don't hit on women who you know are straight. It's rude, and puts you in the same category as straight guys who hit on women who they know are lesbians. Don't be that chick.

On the other hand, there's certainly a way of explaining "oh, if only". I think there's a difference between "hey, I want to jump you" and "hey, if you ever wanted to wander over to the gay side of things, I'd go for you." The former ignores their orientation, and the second provides a slight step-back of "I know this isn't possible now, but should it ever be." Which I think makes it less awkward, and expresses acceptance of their orientation. (Sure, sometimes orientation changes over time or with circumstance, but don't push people to change. Again, that's rude, and puts your erotic desires above their identity.)

But it does sound like you're having bouts of infatuation with women who are - pretty much by definition - unavailable. Which may feel safer, but may not necessarily end up making you happiest.
posted by rmd1023 at 7:54 AM on November 20, 2011 [32 favorites]

My orientation is certainly not anything I would consider a defining characteristic about myself.

For most people, gay or straight, sexual orientation is something that ultimately is a defining characteristic. So women who identify as straight are not going to be interested in dating a woman who identifies as gay unless they are already questioning their sexuality. That's just my opinion.

If you get a signal of interest from a straight-identifying female, go for it, otherwise, it's probably not going to go anywhere and make the person feel uncomfortable.
posted by vincele at 8:02 AM on November 20, 2011 [1 favorite]

I have done similar things before and you have to also accept the possibility that they will treat the relationship as frivolous or ultimately unimportant, no matter what they say or seem to feel at the time, and then go back to being "straight". It's really hurtful.
posted by the young rope-rider at 8:13 AM on November 20, 2011 [8 favorites]

I think your problem is that you're calling your unreciprocated crushes on people "falling in love." Going after straight women is probably ok, as long as you're not pushy about it -- it doesn't carry anywhere near the same baggage as hetero guys going after gay women, and there are probably way more "heteroflexible" women out there.

But characterizing your infatuation with someone -- who might not even be into your whole gender -- as "love" is troublesome. That is the source of your anguish; if you can deal with this, you won't agonize about being rejected by straight women.
posted by modernserf at 8:18 AM on November 20, 2011 [1 favorite]

I think anyone who starts a friendship with someone who they have the potential to date or sleep with let's it cross their minds at least once. So, if you strike up a friendship with a "straight" woman, she may ponder the reality of an actual sexual relationship. If she's curious or somewhere on the spectrum of interested, she can act on that. So, all you need to do is sit back and wait.


Is that really what you want to do? Why pursue someone who is off the table?
posted by amanda at 8:22 AM on November 20, 2011

I'm a straight identified woman who has wondered why her bi and lesbian friends never hit on her. This thread explains it!

I would be flattered if a woman approached me, and likely intrigued. In fact, as things are now, I would likely consider it, provided I found her attractive (I would use the same criteria I do for men). But if she had already decided she was "in love with me", I would be uncomfortable. It would be too much pressure too soon. I would be worried about hurting her. I would want the space and freedom to experiment and explore. Experimenting would be an unfair thing to do to someone who is already attached.
posted by Milau at 8:30 AM on November 20, 2011 [13 favorites]

It feels to me like you're someone who doesn't feel the need to wear your sexual orientation on your sleeve, due to how naturally comfortable you are with it, and you're finding yourself attracted to straight women precisely because they embody that sort of unthinking comfort with their sexuality—perhaps for the women you're attracted to, sexuality is less tied up in issues of identity than it is for many lesbian women you've met. Maybe the answer is to seek out same-sex-attracted women who more confidently inhabit their sexuality
posted by limeonaire at 8:30 AM on November 20, 2011 [9 favorites]

I have a close friend who I only get to see fairly infrequently as she lives on the other side of the world. She is gay, I'm straight. Once upon a time she asked me if I'd ever considered being with a woman because if I was interested then she was interested. I was unbelievably flattered but not even remotely interested. She laughed it off with something to the effect of "it doesn't hurt to ask, right?" and life carried on as normal.

Honestly, it was less weird with her than it has been when a male friend that I'm not interested in has approached me.

I say ask, but do it in a casual way with an easy-out for her. If she is interested the casual question might help open up the topic for discussion. If she's not, then you have your answer.
posted by rubyrudy at 8:32 AM on November 20, 2011 [2 favorites]

What is the point of pursuing a relationship with someone who you know ahead of time will not be attracted to you?

knowing the other woman may be interested sexually can change the level of comfort and intimacy for the worse

I think you might want to examine that statement pretty closely. Because that's not how it's supposed to work.
posted by ook at 8:34 AM on November 20, 2011

How do you know if someone is straight?

My current girlfriend thought I was, for... quite a long time. It kept her from making a move on me. Meanwhile, thoughts like "I don't want to ruin our friendship" kept me from saying anything to her about my own feelings.

Sexuality is a spectrum, and it might not be immediately obvious where anyone falls on it. For the record, I was with a guy for almost ten years, so obviously anyone who knew me then would have assumed I was straight. I myself identified so much with being part of that relationship that I didn't want to claim differently.

Today I am very happy with my girlfriend, and very happy to be able to present a less-than-straight identity.

I guess what I'm saying is - you won't know how someone might respond until you try. Unless someone has made very clear that they are straight/completely uninterested in you, I don't see how there could be anything wrong with casually asking the women you fall for if they might possibly consider dating you.
posted by harujion at 8:45 AM on November 20, 2011 [8 favorites]

knowing the other woman may be interested sexually can change the level of comfort and intimacy for the worse

Doesn't the OP mean "if someone knows that I am REALLY into them, they may feel that we can't just be friends....or if they try to stay friends they may feel deeply uncomfortable or question my sincerity"? Because yes, if someone 'fesses up that they're totally in love with you when you've never even considered getting involved with them it can make things very awkward.

Honestly, OP, I would be more on the side of "ask yourself why you fall for unavailable people...or fall for people where there's huge drama around whether they're available or not". Lots of folks do this and there's a lot of reasons - unconscious fear of intimacy, fear of the boredom of a regular relationship, need to punish yourself, need to believe that you're very different from others (and can't have an average successful relationship), addiction to the drama of being 'in love', etc. Or maybe you're just one of those people who basically loves having crushes and wishing and hoping more than they like relationships. Some folks' sexuality is really about courtly love and pining from afar and so on, and that's okay as long as it's causing more fun (excitement! crushes! wishing!) than suffering (loneliness, embarrassment).
posted by Frowner at 8:50 AM on November 20, 2011 [4 favorites]

This isn't about whether you're allowed to crush on straight friends or not. It's about something else:

- the thrill of the chase - getting that unattainable person x10 because you have to get them to risk something big!

- the stability you get to ensure by crushing on unavailable people, and therefore not risking the chance of true rejection. If you get rejected or turned down here, you get to imagine that is because "she's not gay" not because "she doesn't like you."

- It could be those, but even more likely, I'm getting a vibe of some internalized homophobia / annoyance at all the out queers, who think of themselves as queers and not "too defined by their sexuality". You say you've been out forever to everyone, and this might be a hard thing to consider, but humor me and give this some thought. Do your straight crushes offer some kind of "uncomplicated" portrayal of female sexuality, of normality, of ease and comfort in their own skin? Do the dykes and bois and butches and femmes and lipsticks and leathers and andros and trans folks and fags and studs and all the other (so hot and so queer) gay people you know carry some kind of "energy" and you get the sense that they're making things too complicated? Or that they're more complicated than you feel, or that you want to be, and why can't everyone just be people? Are you annoyed at them for thinking about themselves as gay, and not as you think of yourself, that your sexuality has nothing to do with you as a person? That it's not a defining characteristic about you? That if you're good at your job, and good with friends, and take care of yourself and your family, that why should who you sleep with, or feel attraction towards, be a defining characteristic about you? Why should people tink about sexuality as such an important part of their cultural identity, can't we all just be people with jobs and hot bodies in bed? If any of these things get a twinge of recognition, I really think you need to give this some serious consideration.

Because, yeah, for the most part, we're all people. But growing up as a queer in this world - even in NYC - definitely carries with it an added burden, stress, complications, fear, and you will occupy a particular place in this world as a result. I mean...we're all just people, but hey look! It took massive amounts of energy and many years of surviving a violent biopolitical repression [not to mention a rejection of our queer histories] just to --whew!!-- get gay marriage passed in NY State. So yes, we're all just people. But the gays who refuse to "act straight" aren't doing that just to piss people off, it's because their self-identity is one that has had to be created on the margins. The margins are what they/we were given. It's where we're kept. It's where we're told, maaaaaybe, if you act straight enough, you can pass as straight and not rock the boat, and keep moving ahead. But you have to understand that when the vast majority of these folks say, "screw it, I'm dressing how I want, acting how I want, and screw the world's expectations," that they're not the ones keeping this repression in place. They're owning their political subjectivities. They're not failing to be absorbed into the system, they're sick of being expelled from the system and now claim their difference as a point of pride.

It seems like you've had a fairly easy time being out, but (a) even then, it's something you've had to go through, wrestle with, talk about, come to terms with, and (b) what is it about these overt gays and queers that rubs you the wrong way? Do you wish they'd stop talking about the difference between straight people and gay people, and just get on with life, and blend in? There's so much more to say here, and I'm **honestly** not judging you -- this is such a hard, long, difficult process, and it's one that can come up again in life, and in situations you really thought wasn't a big deal, and then wham! You have to negotiate it all over again. You are where you are, and you'll make it through. But be honest with yourself.

Of course all of this could be totally off the mark. You'll have to wrestle with that yourself. But you underline several times that it's "a mainstream idea to view a relationship – gay or straight – as just that, a relationship" and that who you are attracted to has nothing to do with anything else. I am picking up a vibe that says you're annoyed at those who think and act otherwise, you seem to think it's easier or hotter to convert a straight/normal woman than dealing with those who wear gay identity on their sleeve, and don't pretend to be just like the straights, only gayer!

And if you've been out forever, and even if they're progressive and queer-friendly and lovely, do not assume they'll just glide right into being some your hot gay partner:

a) From where you are, it is hard to imagine the insanity of being back in the closet, but that's what will happen because the person you're dating isn't out (or doesn't want people to know she is sleeping with a woman). This means: friends can't know, gay bars are out, and 8000 other insidious things.

b) Conversely, if you've been out forever, and she decides to come out while dating you, do NOT underestimate what it takes: it's a huge amount of emotional support, mental energy, sexual minefield, not to mention a giant time suck. If you're not prepared for that, it can be a giant mindf*ck. Do you really want to have the conversation about how she can either convince her sister it's an OK thing, or walk away, or "I don't know what to do!!" for the next several months? Year? What about "how do I tell my boss? Does he need to know? What does it mean for my relationships with my friends?"

To all newly out, or about-to-come-out Mefites, this does not at all mean it's in any way inconvenient or annoying to help you come out. Not at all. In fact it's the opposite: when someone *wants* to come out, and lets me into their life in order to help them do so, it's a massive honor and something to which I regularly commit lots of time, energy, emotional and financial resources. But for a gay person to pursue someone who isn't already out, and drag them out or have a relationship with them where they're not out, it's usually because of the thrill of the chase, not because they are committed to that prospective person's longterm emotional psyche.

It takes commitment to being with specifically that person; it cannot be about the thrill of the pursuit, or the thrill of the "illicit" as this case seems to be.
posted by barnone at 9:17 AM on November 20, 2011 [21 favorites]

I think everybody reacts differently to such things. For me, personally, it goes like this: if a casual/friendly acquaintance (woman or man) is flirty, or even quite open about being attracted to me, but manages to do it in a playful manner (rather than lay their infatuation at my feet as though it were my duty to do something with it), I would be flattered. If I am not interested, I'd make it clear though, and expect that person to deal with it. If the flirtyness/declarations stop, all is well, if not, I would begin avoiding that person after a while - it would feel too uncomfortable to be around them. Also, experience teaches that often people who do not stop are untrustworthy - a lot of their seemingly friendly "disinterested" overtures have ulterior motives. Plus, at times it can bring out the bitch in me, too - someone who actually cultivates me having power over them whilst simultaneously trying to pressure me with their feelings and make me perpetually uncomfortable tends to have a negative impact on my behaviour.

If a friend, or even close friend is suddenly obviously pursuing me, I get uncomfortable right away. I try to deflect, hoping to make it clear that I am not interested, and all can be well if things remain unsaid (I do have a friend who more than ten years ago tried to go there. Nothing was ever said outright, and for some reason this makes all the difference - he is still my best friend). However, if I was forced to acknowledge the issue, that would really spell the end of the friendship, for me. I could never see you with the same eyes.

To me, these thoughts apply:

1. If you feel affection for me and value our relationship, you will be as tactful as possible if you try for such a major change both in our relationship and in the way I view you.

2. Before pouring your feelings out and making them my business, do some legwork and try to ascertain how I roughly feel about things like: becoming romantically entangled with friends (some people never go there, and I am one of them), being approached romantically by a friend/a friendly acquaintance/a work colleague (basically all situations which can make someone feel trapped inside of something, giving rise to discomfort and the need to flee - to me, a friendship is like being, together, inside something, like a wonderful and warm and cozy room), being approached by someone you are quite close to who is not of the gender you are usually attracted to, etc.

3. Take things in minute steps, much more so than you normally would. Make your interest known incrementally, giving the other person the opportunity to wrap their head around the idea (or be all over you with enthusiasm, if they get you early on and are completely on board with it). Take a step back as soon as you notice discomfort, and go back as far as necessary for the other person to feel comfortable again (which may well be entirely platonic friendship).

4. Be prepared for low chances of success. There are a lot of stories out there of such things happening (friends to lovers, a sexual-orientation epiphany relatively late in your life etc.), but my feeling is that these success-stories are quite outnumbered by stories of heart-break. Also, generally, if you want to rescue the friendship it may well be you who has to put in most of the effort - whether that is reassuring your friend that you are past those feelings (if you got to the point where you stated them, or even if it was only the case that they were quite transparent), or just suffering in silence once you notice that she is not interested. Also face the possibility that you may lose the friend (she gets too freaked out, or it is too difficult for you to deal with the reality of the rejection/hopelessness).

Saying all this, people are so different that she might have a totally different reaction from what I know mine to be (as is also apparent from what others are saying in this thead). I think your best bet is to put out very delicate feelers. For instance, does she have male friends? Why not ask her how she would react if one of them suddenly confessed his love? Or how she would react if a woman she likes and admires were to suddenly approach her? Initiate several relevant conversations, with quite a bit of time between them, so that she doesn't feel pressured. And then take your cue from her answers.
posted by miorita at 9:38 AM on November 20, 2011 [2 favorites]

anonymous posted">> is every okay for a gay woman to pursue a woman who is straight?

Sure, it's okay. Why wouldn't it be? I'm a straight woman who, back when I was younger and unmarried was sometimes approached by women. I didn't think it was any stranger or more awkward than when I was approached by men.

Think of it more as "I have a crush on a friend, what should I do?" than as something involving the history gay rights in the Western World, and see the bazillion and one AskMes on that subject.

(That you're getting crushes only on presumably straight women might be significant. I leave that to my lesbian colleagues to address.)
posted by The corpse in the library at 9:39 AM on November 20, 2011 [1 favorite]

I think a lot depends on what you mean by "pursue," so here's a general rule of thumb: would it make you uncomfortable if a straight man were to pursue you in the same way? If the answer is yes, then don't do it.

It's fine to say "hey, if you were ever open to being with a woman..." But to continue to pursue someone after she tells you she's straight is disrespectful - it ignores her understanding of her own sexual orientation in exactly the same way that a guy would ignore yours by continuing to hit on you. Just hanging around straight women waiting for them to change their minds, on the other hand, isn't wrong exactly, but it probably won't end well for you.
posted by Ragged Richard at 9:54 AM on November 20, 2011

I would just say this. Think about how you would feel if a straight man hit on you.

If that doesn't overly trouble you, I suppose you could go for it. But be aware that if a gay person hits on someone who is really, no honestly, no kidding straight, it ain't going anywhere. Same deal as when a straight person hits on a really, no etc., gay person.
posted by Decani at 10:41 AM on November 20, 2011

First off, older gay women (who formerly identified as straight) who find one another later in life grew up in a time when being gay was considered more of a deformity than an identity by mainstream society. Basically, the whole of American society was as prejudiced as the Evangelical Christian Right is today, so it's no wonder it sometimes took some of these ladies quite awhile to become ok with dating women. I know you the example you mentioned was from a tv show, but I knew a lesbian couple of about 65 who found one another later in life for these reasons. However, it would be much more unlikely for modern women who want to date women to basically wait a lifetime to do so unless the woman in question was very self-repressive.

As a straight woman who has been sexually pursued more than once by a gay/bi girlfriend, I'd say you're setting yourself up for disappointment if you insist on going after straight women. Although it's hard not to enjoy the flirtation slightly, I flirt with all my female friends in a pretty similar way, very light on the sexual vibe, and it never meant anything more to me when I did the same with my gay/bi female friends. Although I have always said I'd marry my soul mate even if she very unexpectedly happened to be a woman, in the end no such woman has ever shown up, and I have dated men and only men. This has hurt a couple of my gay/bi girlfriends who refused to take a hint.

Also, I'm no expert here, but like so many others on this thread, I'll ask you if maybe you just prefer pursuing/having crushes on unavailable people? There are straight women who seem to have perpetual crushes on gay men, people of all genders and identities who have entanglements with married people, and men who only like crazy, hot women who humiliate them and make their lives hell-- all of these people are prioritizing attraction over common sense/healthy dating behaviors. You may not even realize this is a issue you have.

What's wrong with the single, dateable people who like you, other than they're available and gay? I'm just curious. Is there a particular quality you believe these straight women have that the lesbians you know do not?
posted by devymetal at 11:39 AM on November 20, 2011

Society isn't saying they're off limits, they are. You might get lucky once in a blue moon but mostly you're just going to lose a lot of friendships. There's a lot of gay girls out there and I think you're just going to make life hard for yourself and - more importantly - those around you if you keep going down this route.
posted by joannemullen at 12:22 PM on November 20, 2011 [1 favorite]

So, you think that people are talked into their sexuality? I'm sure you don't really think that.

It occurs to me that if you are always attracted to people who are completely unattainable, you never run the risk of being hurt. Something to consider.
posted by Houstonian at 12:33 PM on November 20, 2011

It is generally rude to hit on people who have let it be known - through orientation, relationship status, semiphone, whatever - that they are not available.
posted by DarlingBri at 12:35 PM on November 20, 2011 [1 favorite]

There's a difference between expressing interest in a woman who's never dated another woman and expressing interest in a woman who has told you, "I'm straight" or "I only date men." If a woman has explicitly told you she's straight, then it's rude to pursue her. If she hasn't, then it's not.

Sure, there are a lot of women who identify as straight until they don't. But that doesn't make it ok (or productive) for you to question other women's sexuality for them.
posted by Meg_Murry at 12:36 PM on November 20, 2011 [2 favorites]

Although not answering your question, just an observation: do you think that you falling for straight women might be a subconscious method of protecting yourself? No matter how much you "fall" for them, you know you can't get involved. It's like falling for someone who is married and never leaving their spouse, or falling for someone and "it's complicated". Crush all you want but, at least subconsciously, you know that nothing is going to happen between you two.
posted by Neekee at 12:53 PM on November 20, 2011

I actually know several women who did and still do identify as "straight" - but are now in long-term, committed relationships with women. A few have said they probably wouldn't be with a woman if the current relationship ended. Most of these relationships have lasted decades.

All of them have said the same thing: they fell in love with the person. Were they more in the middle of the Kinsey scale than they had realized? Who knows.

My advice would be to not pursue straight women - but take the temperature of the friendship once in a while. If you get the feeling at some point that maybe things are developing - then go for it. Just be aware the friendship could end or change. I'd wait until you're ready for it to be all or nothing - or to weather a small, uncomfortable storm.

Assume the answer is going to be no. Assume she might be up for a little experimentation - but not for the long haul. After all that and you're still hot for her? Go for it.

I also think you should take your own temperature - do you like straight women for the thrill of the chase? Because it's "safer" emotionally? Being attracted to people who are not available (for any reason - married, straight, whatever) is probably just not in your best interest. And it's much easier to romanticize what could be with someone it won't ever be with. Just like men who cheat - sometimes they do leave, but the odds aren't great.

But if it's not a pattern - and I don't know you, so I won't assume it is - let the friendship run its course for a while.

FWIW, even if it is a little "predatory" - who cares? Don't be a shithead, be gracious about rejection and be willing to laugh a little about it later. Just tread lightly in friendships you value.
posted by crankyrogalsky at 1:00 PM on November 20, 2011 [3 favorites]

First, have you ever had any sign she was attracted to you? Is she the type to get offended or weirded out?
I could tell you to bisect your feelings and figure out what is going on and your motivations--
--but if you go for it, let it come up naturally and lightly, perhaps comedically, in a way that can be brushed off, sidestepped, or ignored. Maybe just complement her and see her reaction. Lots of little things can express your interest in an inoffensive way, and leave her open to respond.
Be aware you may end up as an experiment and your friendship may not survive.
If it does work out, then there are a whole other set of issues to deal with, and I wonder if you've thought that far. Have you ever been in a serious relationship before?
posted by provoliminal at 1:04 PM on November 20, 2011

Sounds like you need a bigger dating pool, but you are going about it in a way that is unlikely to succeed. I'm curious -- do you actually hang out where lesbians hang out, at least sometimes? Maybe in some sense a relationship is just a relationship, and falling in love doesn't require a particular identity or label, but one of the reasons that there are lesbian book clubs and lesbian softball teams and lesbian bars is that these venues maximize the chances of meeting someone compatible. If you think that your life goals and experiences are so unique that no lesbian could possibly share them, I wonder if you know that many.
posted by Wordwoman at 1:06 PM on November 20, 2011 [1 favorite]

I'm regretfully straight in my physical orientation, as I discovered when I was hit upon by a much younger woman friend. She's married now. We're still friends and not the least uncomfortable. It was a move of comfort that she made when we were talking about the painful things in our lives. Perhaps this is something that happens spontaneously in the moment of closeness rather than anything so carefully considered. It was not rude.

What concerns me more however is this bit that another commenter has written:

But it does sound like you're having bouts of infatuation with women who are - pretty much by definition - unavailable. Which may feel safer, but may not necessarily end up making you happiest.

Is there a pattern here you might want to take a closer look at? I went through a similar pattern after my divorce where it took one of my best friends to point out to me that I kept falling for very unavailable men and then proceeding to have long fantasy crushes on them - it was safe and kept me safe.
posted by infini at 1:10 PM on November 20, 2011

My question is this: when is okay, or is every okay for a gay woman to pursue a woman who is straight? For those ‘straight’ women who are now with a woman or were ever with a woman, how were you approached?

But as I get older, as I continue to fall for women whom society once said were off limits, I am more and more curious to know if and how this is changing.

Wait, wait wait.

There's a note of something here that strikes me as maybe not totally respectful of these women. In the first sentence you asked about pursuing straight women, but after that, you have "straight" in scare quotes.

People usually use scare quotes on a word to challenge it in a way -- to indicate that they're using it ironically, facetiously, etc., to indicate that they believe the word should not be used literally in that context. It makes it seem to me that you're not taking these women at their word that they are straight, or not respecting it, or you see it as like a mistaken idea that they have that you could show them the truth about.

If a woman tells you that she is straight, the respectful thing to do is to take her at her word. I would find it unbelievably offensive if a straight man asked us, "Is it okay for me to pursue 'lesbians,'" using scare quotes like that.

I think it would be fine, just like in a friendship between two opposite sex heterosexual people, to let your friend know ONCE about your feelings for her, and then leave it alone after that and be normal if she doesn't feel the same way. Pursuit of someone in that situation, and ignoring what she's expressed that her sexuality is, seems really disrespectful.

As to this:

But as I get older, as I continue to fall for women whom society once said were off limits, I am more and more curious to know if and how this is changing.

If straight women aren't interested in dating other women, it's not because society is saying they are off limits, and their true desires are just be restricted and oppressed by society. They're not interested in dating other women simply because they don't want to.
posted by cairdeas at 2:04 PM on November 20, 2011 [1 favorite]

If you've never had a discussion with them about their sexuality, I think it's cool to do so. You might be pleasantly surprised. For example, I identify as straight, because I have only ever had heterosexual relationships, and because 90% of the time when I am attracted to someone, it's a guy. But I do get girl crushes too, and I would be totally open to pursuing something with someone of the same sex if it was the right person at the right time.

I think there are more women out there like this than some people would expect. So just because your friends identify as straight to the world, doesn't mean they wouldn't be interested in you under the right circumstances. But before making a move, I think it would be better to have a talk about their feelings towards women. Get a little bit drunk together one night and start talking about crushes, or about the nature of heterosexual/homosexual desire, and you'll get your answers.
posted by lollusc at 2:22 PM on November 20, 2011 [3 favorites]

My question is this: when is okay, or is every okay for a gay woman to pursue a woman who is straight? For those ‘straight’ women who are now with a woman or were ever with a woman, how were you approached? For those gay women now with (or were with) ‘straight’ women, how did you know when it was time to make a move, assuming you were the one who did make the move?

This is the easiest question ever, dude.

Change "gay woman/woman" to "hetero man".
Change "straight" to "gay".


At what point would you consider it not OK for a hetero man to pursue you? THAT is the point you should not cross with others.

Good luck.
posted by hal_c_on at 4:23 PM on November 20, 2011 [1 favorite]

For those ‘straight’ women who are now with a woman or were ever with a woman, how were you approached?

By respecting why I identify as straight.

So, like: I've slept with women, dated women, and there was sexiness and fun, but the truth is that I am not romantically attracted to women. At all. The sex? Hot, hot, amazing, fun, great, wonderful. The dating? Meh. And with no future (in my mind), because I can only envision love and partnership in terms of it happening with a man. I just don't experience the same emotional depth with women that I can with a man.

So, when I was younger, I did some dating and experimenting but was pretty honest fairly quickly that a relationship was not really going to work for me. Things were going to have to be casual, or maybe as part of a m-f-f threesome experience. I was sometimes not taken seriously by the women I dated, though I was being honest.

Even though I still consider sex with women to be wonderful, I no longer get involved with women because A) I am not currently interested in casual sex B) I am in a monogamous relationship with a guy and c) this situation has led to hurt feelings. Things might be fun at first, but really: there will never, ever be a future for me and a women. It's just how it is, so now I just hang out in the hetero camp.

So, it's something to keep in mind, and might be good to keep in mind with women who truly don't ever envision themselves being with women, in any way.
posted by sock puppet of mystery! at 6:43 PM on November 20, 2011 [1 favorite]

As a woman who has identified as lesbian, bi, and straight, at different times in my life, I'm going to give you a long answer.

1) When I was lesbian-id'd, I was grossed out by men who hit on me despite the fact that they knew I was gay. As a now straight-identified woman, I'm not into women who know I am straight trying to get with me. Just like when I was bi-identified, and in a monogamous relationship, I was not cool with people who knew I was taken trying to hit on me. It's a respect thing.

2) Really never never never believe you can change someone's sexual orientation. You can't. Just like a really awesome smart charming hot guy isn't going to turn you bi or straight. (Like they say they can in those creepy "ex-gay" religious programs.) You're gay. Some people's sexual orientations can be in flux over time, especially women's--there is research and I'm living proof--, but the timing of that flux and change is not up to anyone else. You can't force it.

3) I worry these straight women are going to continue to hurt you and let you down. Where are you going in the city to meet women? There are a lot of amazing gay women out there. Try meeting them at different venues, straight, mixed, or gay. Gay: Everyone is very friendly at Cubbyhole. Mixed: A lot of bi & gay women in NYC are on OkCupid. Try volunteering for an LGBT or women's org/event. Straight: More importantly, try a volunteer gig at an org that inspires you. With the # of gay women in NYC, you're sure to have a good chance of finding a lesbian who shares your values and interests there.

At the end of the day -- work on yourself before trying to change other people. You need to figure out why you are so into these unavailable women. I don't think this is about being gay at all. I think the unavailable thing might be the crux of the issue here. Your pursuing uninterested straight ladies can be in a way predatory to them, sure, but it also can be a danger zone for you: years of hurt and unrequited loves. Take care of yourself!
posted by manicure12 at 8:05 PM on November 20, 2011 [2 favorites]

I think I might be the type of straight woman you keep hoping your friends might be, so perhaps I can offer a little insight.

I am not 100% straight. I've never really thought I was. Thing is, for a long long time I only dated/flirted with people who pursued me first. I never had the confidence to initiate. I also 'read' as very, very straight, so those people were always men. I was very happy dating men, very turned on by them, so I was sort of straight-by-default. But I've always been attracted to women, and, at least in my fantasies, very interested in sex with them.

You might wonder how or why I've never tried to explore that aspect of my sexuality. Well, I usually explain it like this: You know that feeling you had back when you were totally inexperienced and had no idea if you were doing anything right and were petrified you'd "be bad" at...whatever? Yeah, I got over that with guys, but I never had the experience to get over that with women. And I was too afraid of feeling that way again to actually pursue any women. I always hoped that some cute gay girl would hit on me while at a party and I could explore in some meaningless, futureless situation, where the consequences of being terrible at...whatever...would seem pretty insignificant. But, er, it's never happened. I move in circles that include many gay and bi women (and men, for that matter), but no one has ever made a move on me, or even flirted that hard. I mean it, until the last year or so, no gay or bi girl has EVER made any kind of move on me. Even flirting has been the "haha you're so straight! it's too bad!" sort. Even when I'd reply with "Well, I don't know, maybe I'm not! It's never really come up!" I'd get a response along the lines of "Haha, aww, riiiiiight." And well, I never had the confidence in my skills with women to correct anyone.

So it would seem I'm JUST what you'd hope your friends might be. Most people who know me think I'm completely straight, but I'm comfortable dating women, intellectually, and would be comfortable coming out as bi if I were dating one...but what I'm really UNcomfortable with is doing this initial exploration and learning with someone who's already a good friend. The stakes there are just waaayyyy too high. I can't even fathom dating a gay friend who's expressed deep romantic feelings for me. I'd be far too worried about hurting her to relax and just enjoy the experience. Most likely, if I got the feeling she cared for me that way (as opposed to just thought I was hot and would like to make out) I'd discourage her without ever disclosing that I was attracted to women. I'd actively hide that with stakes that high.

So, everyone's different, but I agree with the other posters who say this is very unlikely to ever end well for you (assuming you know this friend of yours identifies as straight; if you're just assuming she's straight, by all means, ASK). There are all sorts of women out there. My gay friends are wonderful and amazing, and, well, a lot like my straight friends. We're all friends because we get along, we like similar things, have similar views on the world, etc etc blah blah blah. Other than who they date, there's not much that distinguishes the gay wmen from the straight. I can't imagine what could be common only to straight women that would make them better matches for you. I think that's probably something you need to untangle for yourself.
posted by JuliaIglesias at 9:27 PM on November 20, 2011 [2 favorites]

Since sexuality is often a very private kind of thing, I'd consider the possibility that not all women who seem to "present" as straight are always straight. Also, given the way our culture sees bisexuality or fluidity (that is to say that it's kind of taboo, hidden, and even less acceptable than being gay--"just pick a side already!" etc), you may not always know if someone is interested in both genders (and they might not know either, although I'd heavily caution against presuming you understand someone's sexuality better than they themselves do). I think sexuality is far more fluid than people give it credit for. Not to mention that not all "straight-presenting" women are going to know you're a lesbian unless you make it obvious.

I disagree with people who say it would be upsetting for a straight woman to have a lesbian friend express romantic interest, that just seems narrow-minded to me. However, I wouldn't recommend this course of action with a long-time best friend because it could be catastrophic (as in, why didn't you tell me earlier, now things will never be the same, etc). I'm thinking more casual friends or acquaintances. I agree with hal_c_on who said that you should use what you'd tolerate from a man expressing interest in you as your barometer for what is appropriate and inappropriate. As long as you're respectful, I don't see the harm in taking a chance that the other party shares your feelings but has never dated a woman before, etc. I'd take the same types of things into account as you would with any friendship you're trying to assess for romantic potential--be aware things could go badly and you might lose a friend. You have to decide if it's worth that risk.

All that being said, I still think you might find it less frustrating to try and network with other lesbian/queer/bi folks. Anything relating to marriage rights, LGBTQ pride/activism, gender-equality, reproductive rights, NOW, etc. is a great way to meet other wonderful women in your city, and the concentration of them who are lesbian/bi/queer/etc is likely higher than any other grouping of women. I'm also in agreement with those who have suggested you look deeper into your motives to assure you are not in a cycle of attachment to those most unavailable to you. Lastly, I'd also agree that you shouldn't paint lesbian women with such a broad brush! It's unfair to assume they're some monolithic group you find boring as a whole. Lots of fish, etc.
posted by araisingirl at 9:38 PM on November 20, 2011

Just piping up here to nth the notion that appearing straight and being straight are not necessarily the same. At all levels, I look totally straight. But I've felt what I can only describe as love for other women that I've never acted on and wish I had, and if any of them had given me the slightest hint that they'd shared those feelings for me, things might be very, very different today. I can't say the same about men, though, because once you appear straight, striking up hetero relationships is a whole lot easier than striking up gay relationships if you're not seen as gay.
posted by Capri at 10:58 PM on November 20, 2011

seconding SUPER RUDE. I am a straight woman and had a gay female friend hit on me repeatedly when she would get drunk. It just made me not want to be her friend anymore.

If someone you had been clear with about your lack of interest kept hitting on you, how would you feel? It's a betrayal of trust, it's creepy, and it makes you a shitty friend. Don't do it.
posted by custard heart at 9:25 PM on November 21, 2011

Forty answers already so I can't think of anything that hasn't been said. As a gay man, my two most important points would be:

Pursuing a straight someone-you-care-about is generally masochism at best.

I agree with the cultural shift; there have certainly been more than a couple men who I've knocked off the fence. (Those have been more short-term things/wasn't something I wanted to pursue.)

Almost contrary to my first point, I would insist on at least initiating dialogue that would provide a clearer answer. If you're close already, it won't be unexpected or make things very awkward. If you never ask, you may always wonder about possibilities.
posted by at 2:42 PM on January 21, 2012

And I second lollusc's advice.

For what it's worth, that's exactly how my roommate and I started hooking up. I posted an ad on craigslist with no indication of being gay and he was the first to come with money - he agreed to sign after a few short emails, before we even met.

It reminds me of one more bit of advice - let them chase you. If you come off as anything further than 'open' to the possibility, I think it might work against you.
posted by at 2:50 PM on January 21, 2012

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