She Said, She Said: Advice About Dating Ladies and Having a Bad Sister -The Toast

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Previous installments of The Toast’s advice column from two disparate and imperfect persons can be found here. Last time: Dating Disclosures.

My sister is a blonde, blue-eyed white girl and just went away to college earlier this fall. I just found out that she wants to transfer to go to a “less urban” college. 

She’s actually my half-sister, via my father and stepmother, but we typically don’t make this distinction in my family. Due to our 12-year age difference and the fact that we didn’t grow up in the same house (I lived with my mom and visited my dad for summer/holidays), we aren’t super close. We talk on the phone occasionally, text, and I of course visit her when I visit that half of my family. She lives in Texas, which I wish was not such a key part of this situation, but I fear it just is.

We’ve chatted a few times since she went away to college about her part-time job, classes, and missing her boyfriend, who attends a different school a few hours away. I was surprised when I talked to my dad a few weeks ago and he mentioned that she is working on a plan to transfer to a new school. The first red flag to me was that she wants to transfer to her boyfriend’s school, which…eww in general. It’s also not as academically challenging and my sister is very smart. The second red flag was much, much worse–she feels uncomfortable with all of the black, Hispanic, and gay students on campus. Her plan is to transfer to this other school, with is much less racially/ethnically diverse and located in a rural area. My dad is basically like “I don’t want her to be miserable” and “It’s too much of an artsy atmosphere to have anything for her socially” and is caving to her desire to transfer. 

I really want to talk to her about this. I’m just not sure what to say when I get her on the phone. 

Nicole: Oh, man, this is a pretty shitty situation. I’m of two minds, honestly, the first of which is “it seems like you do not actually have much of a relationship with this person, and maybe you could just embrace that and let her spin out on her own and not get bogged down in her ish,” but, hey, she’s a tiny baby person, and it sounds like she’s hitting a culture shock wall, and you love her and you’d like her to be better. We have to believe that people can become more interesting, more open people, or we’d just withdraw into our little blue enclaves and…oh.

What’s your dad like? Is your dad more like you, or more like her? If she talks to him a lot, that might be a nice inroad into feeling her out on this stuff, since it seems like you currently have a more casual, text-y relationship, which doesn’t lend itself as well to “let’s talk about the gorgeous rainbow of human diversity.” I’m also asking because what you’re hearing right now seems like you’re getting it from your dad, and not directly from your sister.

My third and strongest mind, which has come to me on re-read, though, is “her boyfriend’s school.” I’m sure she’s frazzled by encountering different types of people, but I think what we have here is also a classic case of not wanting to have to break up with your high school boyfriend, who you are going to wind up breaking up with.

Call her, and ask about him, and how’s she’s feeling about it. I think there’s a decent chance that the other stuff will shake out on its own as she goes through the great school of life, and this particular transfer-request is rooted more in a fear of being on two rapidly-separating ice floes, and trying to find ways to justify the move without saying “it’s for this dude.”

Mallory: Oh, dear. I don’t know about you, but I can generally smell a conversation that’s designed to change my mind from miles away, especially when it’s initiated by someone who normally doesn’t call just to say hello. Do feel awfully free — in fact I think I would encourage you — to become somewhat more of a presence in her life, both because having a sister can be quite a lot of fun and also so you can set a Shining Progressive Example, but divest yourself immediately of the idea that you can convince her not to switch schools to be closer to a legion of Caucasian boyfriends, or whatever. If she hasn’t already learned that white people aren’t at our best in groups, she will soon enough. (We can be so great one-on-one, sometimes! What is it about bringing us together that just sucks eggs?)

I think it’s a good and a lovely idea to try to become a bit closer to her, and I think it would be perfectly appropriate to call and tell her you heard she was thinking about transferring, and to ask her how college has been treating her so far and where she wants to go and what she wants to get out of it. But I don’t think there will be much you can do or say at this point that will influence her decision.

Maybe transferring schools will be a terrible decision; maybe it will be her Racist and Homophobic finishing school. Maybe she won’t transfer at all; maybe she’ll transfer and break up with her boyfriend five weeks into the spring semester and get really into psychedelics for a few months and mellow out and start a queer literary magazine. Anything can happen in college.

So. I’m a woman, I’m 24, I’ve spent the last twelve years cheerfully dating and mooning over men, the last eight years fucking them, and the last…five? we’ll say five…months abruptly and more than incidentally attracted to women. Which is fine! I’m not existentially devastated, or consumed with self-loathing. I mean, my lesbian friends are at the point where they’ve started experimenting with men, which makes me feel behind the curve, but no one in my life would have a problem with me dating, fucking, and/or mooning over women (although coming out does seem…tiring). 

I guess my question is…is this normal? Is it…a thing that happens? Does your sexuality (well, not your sexuality. My sexuality. One’s sexuality) up and change more than a decade after puberty? And if it has, now what? Is it fair for me to start dating women while this is new and a little confusing? How much of the above should I disclose if I start seeing a lady–can I just pull a “Haha, this will be highly experimental!” before going down on her? I feel so stunted.

I don’t know why this is embarrassing, but it is (please picture me covering my face with my hands after each sentence). My family is so liberal! I’m so well-adjusted about sex! Why didn’t this happen earlier? What is wrong with me? UGH. I would love to hear what you and your brilliant readers have to say.

Nicole: Is there any chance you rear-ended a lesbian witch-crone figure with your car, and then she stroked your cheek with a fabulous talon and said: “gayerrrr”?

No? Okay, this is definitely a Mallory question. My advice is hopelessly generic and is all “go for it, tiger, be honest and transparent and do not use people as experiments, but if you want to kiss someone and that person is into it, godspeed.”

OH, I do feel very, very confident in saying that you should not say anything about the mysteries of your first oral encounter with a woman during the experience itself, though. No references to The Descent, especially.

Mallory: Oh, it’s fine! It’s fine. I mean, don’t ever use the word “experimental” with a woman who dates women, but the rest of it is fine. There are just boatloads of gay and bi women who feel like they got hit over the head with the Lesbian Hammer comparatively late in life, and that they need to catch up to all the real dykes who were playing bass and wearing rainbow bandanas in the eighth grade.

If I had to guess, I’d say as many as 45% of us are all wandering around the edges of the party, drink nervously in hand, too terrified to look at one another because we’re all convinced we’re the Least Gay Woman in the room. (I have no idea where I got that percentage, but you know what I mean.)

Also: your lesbian friends are already hitting their straight phase at 24? Are you living in Logan’s Run? Are you nearing death? Do you need help escaping Carousel?

But it’s fine. You’re fine, everything is fine. Go out with some women. Keep it light, keep it fun, try not to have more than two drinks on your first date, if drinking too much on a first date and thinking you like someone more than you actually do is a problem you sometimes have.

I don’t know why it hasn’t happened earlier for you; I also don’t think being “well-adjusted sexually” is necessarily a fixed and universal thing, since having sex is an entirely distinct proposition with each new partner, so don’t feel worried that you weren’t so well-adjusted you didn’t adjust yourself into homosexuality at the age of nine. What has happened has happened; what is happening now is happening now, and it’s fine. Being a lesbian isn’t necessarily like joining the Jets; you’re not one all the way from your first cigarette to your last dying day. You’ll have particularly gay days; you may have particularly gay years or relationships or seasons or afternoons, and there’s nothing to be done about it. Date as many women as you find yourself interested in for as long as you like. Be honest, be kind, and be patient with yourself and with them in bed. You’ll figure out what works for you and I am sure you will find yourself with as many receptive, communicative, enthusiastic lesbian sex chums as you desire.

One of my old college friends was a thousand-yarder — the kind of lesbian you can spot from a quarter-mile away, which is one of the best kind of lesbian — who fell in love with her straight best friend. They were so damn precious together it made you want to move into the woods and start talking to animals. But we were all a little nervous for the first few months (“She wears eye makeup and has a real case of straight voice and it’s not that we don’t think she loves you, it’s just what if some tall guy named Chad comes along? No one can compete with a tall guy named Chad”). Reader, they have been together for five years and recently got engaged. They are disgustingly happy. They go to pumpkin carvings and do scrapbooking and rescue dogs and make out in front of waterfalls and they are just crazy for one another. I don’t know what this anecdote was supposed to illustrate, other than the fact that I’m a little jealous of my old college friend’s relationship. Maybe it’s just this: there are many paths that lead to lesbianism. Some tarry there for only a short while before returning to the sunlit fields; others make their home there forever in the sisterhood of womyn. It’s all great, though. Look at Krisbians.

It’s my belief that everyone has the right and the duty to be as gay as they possibly can. Not as gay as you think you should be; as gay as you are capable of. This may mean dating a few women, eventually taking a husband to your bosom, but always supporting shows with lesbian characters, or occasionally looking at femslash on Tumblr, or maybe even just loudly proclaiming that Kate McKinnon is your favorite SNL cast member. The important thing to remember, I think, is that you can be just as proud of being a little bit gay as you would be of being enormously so.

Think of lesbianism the way flight attendants for Southwest Airlines think of your business: “Whether this is your final destination or just a stop in your journey, we know you have your choice of airlines and thank you for flying Southwest.” It’s perfectly fair to date women without knowing whether or not you are ready to settle down with one for the rest of your born days. Just be straightforward and don’t build up someone’s expectations if you don’t intend to follow through. That’s just a good rule of dating. Not even lesbian-specific.

I will now generalize grossly from my own experience dating women: even the least successful first date I have ever been on was tremendously pleasant. We had coffee and then looked at shoes together (I KNOW). Women, by and large, are very nice and make for splendid listeners. I’m sure there are exceptions, but I don’t happen to know any. Women will be painfully kind and respectful if they decide to turn you down, and women will almost always show up on time when you’ve made plans together.

So: be honest about your history, by all means, but don’t make it the first thing a prospective date learns about you. You’ve been dating for a while, sure, but you’re also only 24; you’re not exactly a late-in-life dyke bloomer. Plenty of bisexual and lesbian women haven’t had their first girlfriend or hookup by their mid-20s. I am very Old; I am going to be 27 next week. I should know.

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