You Need Help: I Can’t Figure Out What I Should Wear and Who I Should Date

Q:

Something I’ve struggled with throughout my whole (not so grand) dating history is the fact that I can’t really place myself within the structure of lesbian dating. I’m physically hour glassed shaped, but feel uncomfortable with overtly feminine presentation, at the same time I’m not drawn to more masc presenting styles. I also fluctuate in type, all my past relationships have been with femme women (who I was very much attracted to), but my major crushes, that I didn’t gather the bravery to pursue, were mostly masc of center. I can’t figure out who I want to pursue, who I want to be, and how I want to present myself. I’m a little older and I still struggle with being “butch” enough to swipe on a hot fem girl, or “sweet enough” for a classic “top.” I’ve been told it should feel natural. People always talk about how as part of coming out you “dress/act as who you truly are,” but how do you proceed when every outfit feels like a costume and every date you go on a performance?

A:

I just let out a super long, emotional sigh. I can very deeply relate to the questions you’re asking yourself. Even though you would think that we as a queer community could have collectively come to the conclusion by now that specific dating stereotypes, like the idea that everyone must pair up in a butch-femme dynamic, don’t need to be followed, it often feels as though there is still only one specific formula to follow when it comes to queer dating and presentation, particularly when you don’t see yourself fitting into any box neatly. This becomes even more confusing when you factor in your relationship to your body, your personal style, and how you want to present yourself to future lovers. I’ve been told the “just be yourself” and “dress in what makes you comfortable” thing, but those questions always drive me crazy because I can never quite answer them; I don’t feel comfortable in femme clothes or super masc clothes, especially because I’m also hourglass shaped, which makes me feel high femme when I’m wearing anything femme of center, and a little dysmorphic when I’m trying to appear more butch. And then, there’s the question of who I want to attract; Should I dress more butch because I want a femme girl, or should I dress more femme to attract a soft butch? It’s at this moment when I attempt to pause my racing thoughts by staring in the mirror and recognizing that I’m operating from a place of assumptions about “what a queer couple should look like” that aren’t true, but knowing and feeling are two totally different things.

So what do we do when we can’t figure out how to feel like ourselves and we can’t even figure out who we’re attracted to? I’m on this journey with you, and while I wish I could wave a magic wand and give you super confidence and the perfect partner, we all know that even gay magic has its limits. I will share, however, a little part of my journey that may shed some light on finding identity within queer dating.

Over the past few years I’ve been hellbent on looking and feeling more butch and putting “top” energy into the world. I changed my whole wardrobe, switched who I was swiping on, and started being the aggressor in relationships. Similar to you, I felt like I was performing certain parts of who I was, or wanted to be but I didn’t really know why? Because of this, I always felt like my very real love of “softer” or “straighter” things like Disney princesses, musical theater, and Taylor Swift was too femme for my public dating personality, so I would hide it strategically. At first, I would just enter into dates and sexual encounters by asking the other person questions, but soon I found myself swerving frantically around topics like weddings, family, and emotions, sensing that in order to be the “cool” top, I needed to engage in emotionless sex, hate my family, and hate the institution of marriage. While all of these things are totally fine and great for other people, they are definitely not me. I’ve realized that I’m not actually happy with this aggressive persona I was trying to create because in all honesty, at the end of the day I’m still a head-in-the-clouds dreamer who wants to be proposed to at Disneyworld (I know, I know). This doesn’t mean I can’t be masc and love all of the things I love, but it made me realize that I should be the person who will attract someone I actually want to be with because they like the authentic me. To put it more simply, I don’t want to attract someone who only likes me because they think I have “cool” taste in music or because I told them I want to live off the grid just so I can sound impressive. Ultimately that would end in heartbreak for both of us.

So, I guess I have some questions for you. What do you want from dating apps? What do you want from dating? How do you want to feel about yourself when you look in the mirror: sexy, confident, cute, smart, all of the above? By naming what you want from a specific tool or outfit, it might give you clues as to how to feel more true to yourself. For example, if you’re using dating apps to find a long-term partner, it might be helpful to envision the mental and emotional qualities you want in a long term partner and how you imagine you’ll feel when you’re with that person. From there, you can navigate through people who have those traits. If you’re going out for a night and want to look hot as hell, think about the last time you felt hot, and then think about why. Was it because you were surrounded by your supportive friends? Or maybe because you had on really comfortable shoes that let you dance for longer? “Hot” doesn’t have to mean leather jacket, low cut shirt, or ripped jeans. When you name the feeling you want to have for the occasion you’re dressing for, I encourage you to notice things that feel familiar and good, and go from there.

It’s TOTALLY okay to feel sexy in a cut-off one day and then fly as hell in a dress the next. It’s okay not to cut your hair or wear lipstick. Even though it feels like these are simple reminders, I’m partially writing this to also remind myself that it’s okay! We don’t need to have one particular vibe, type, or style. Furthermore, it’s totally valid to present masc and be with someone masc presenting. It’s valid to present femme and be with someone femme presenting. It’s valid to be androgynous presenting and be with someone androgynous. When it comes to queerness, no rules apply! We don’t gatekeep! Go for the hot butch if you want! Even if you find it difficult to let go of labels and static dating roles, I would encourage you to just take the next step that feels right to you in this moment. You don’t have to have it all figured out now, next week, or next year. When the time comes to hit on someone, swipe on someone, be “yourself” on a date, or dress yourself, think in really small steps: what feels good right now? What should I say in this moment that is true to me? Don’t worry about what will feel good in 20 days — you can think about that then. Trust your intuition in all of the small steps and I guarantee you will lead yourself closer to a you that feels more authentic.


You can chime in with your advice in the comments and submit your own questions any time.


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Em Win

Originally from Toledo, Ohio, Em now lives in Los Angeles where she does many odd jobs in addition to writing. When she's not sending 7-minute voice messages to friends and family, she enjoys swimming, yoga, candle-making, tarot, drag, and talking about the Enneagram.

Em has written 16 articles for us.

7 Comments

  1. Just want to second everything that Em said! Also want to chime in on a personal level, since my presentation has evolved a lot over the years (I’m now in my 30s).

    Overall, I would say it’s very rarely worth it to try to change how you dress/look/act just because you think that’s what you need to attract the kind of person you want. That’s not to say that experimentation for its own sake is a bad idea—you never know what’s going to feel good until you try! But once you do have a sense of what feels good: stick with that. For me, nothing has been more wonderful than finding people who are drawn to the same version of me that I like the best. I am much happier with a “smaller” pool of people who are into what I have going on, because that pool is full of much more exciting and sexy connections. Humanity is VAST and WEIRD and IDIOSYNCRATIC—there is no way for you to move through the world that won’t be exactly what SOMEONE (and probably quite a few someones) is looking for.

    I’m not sure how old the letter-writer is, but I’ll also say that feeling of everything being a performance and a costume started to fade more and more once I was about 25. Things feeling messy doesn’t necessarily mean you’re doing anything wrong. Keep playing around, and focus on what feels good to you, not what you imagine someone else would want. I’m rooting for you!

  2. So many people in the queer community have imposter syndrome. Sure SOME people effortlessly fit into certain roles but even more people don’t fit neatly into Butch/femme, top/bottom, WHATEVER role we’re talking about. Plenty of people who seem like they do are at least partially faking or suppressing parts of themselves to fit where they think they “should” in the community. I don’t think this leads to happiness or authenticity for anyone.. do what makes you comfortable. Be your actual self. Forcing yourself and others into neat boxes to avoid contradiction and nuance is not the way. Trying to present in certain ways to attract others is dishonest, hard to maintain in the long run, and leads to resentment on all sides. Whatever mix of things you have going, there are tons of people who will be down with it. And being your real self gives others permission to do the same. It’s a win/win.

  3. In college and soon after I always felt like the other chicks got some sort of memo about how to dress that I had missed out on. I’d think I looked great, then show up at an event and realize that I was the odd person out. What helped me was deciding that since I’m bad at looking like everyone else, I’ll commit to always looking like the best version of myself. That would be my suggestion for where to start – what are the item/s in your wardrobe that make you feel like the best version/s of yourself?

  4. Hi anon! This has been a feeling I have related to in the past, for much of my life I’ve felt a stranger to myself when it comes to self-expression, but in the way there are some things I figured out, that hopefully would help you in some way.

    The thing about queerness is that this feeling of “performing” is a theme that follows many of us, but on the other hand, this illusion of mandatory “finished-ness” is an illusion coming from the part of society that has always wanted to police our expression anyway. We all are works in progress, despite how some want to keep a polished front that hides that fact; it’s alright to not have found a definitive style yet, it takes time for those of us who are punished in some way for self-expression, whatever it is, and it’s best to do justice to this fact by focusing on what feels good to you, step by step.

    As for the dates, I understand this is a scary option if unpracticed, but wearing your “work in progress” on your sleeve as a source of further curiosity can be attractive, too! There is a daring quality in being upfront about it and go “hmm. what if?” that I’m sure many would appreciate; there are times pretension alienates more than it brings people closer. In case someone gives you crap for this, that only means you two weren’t a good match, it’s no reflection on your journey.

    Sending good vibes your way, and good luck!

  5. It sounds like the letter writer knows exactly who they’re attracted to! They say they were very attracted to the femme girls they’ve dated in the past, and have big crushes on butch girls too. So, they’re attracted to butch AND femme girls – and I have a feeling most queer women are in the same camp in terms of being attracted to a range of gender presentations regardless of their own presentation. Good news then, you don’t have to dress any particular way to attract a butch or femme woman, because not all butches like femmes and not all femmes like butches. I actually don’t think the majority of queer people prefer partners who present “opposite” to them. Probably just as often, people dress in ways that mirror what they themselves find attractive, or what they find attractive in others is influenced by what is attractive in society at large (especially as queer culture becomes more assimilated into mainstream culture).

    On that point, despite how unrelatable I find the focus on butch/femme dynamics in the letter to be, the whole idea of presentation and attractions being pushed into a box because of weird expectations IS relatable for sure. I’ve got my own set of almost “opposite” hang ups to the letter writer! Like, I’ve found myself swiping left on super feminine women, or not messaging them, because I’m not feminine ENOUGH…I’m afraid they won’t be attracted to me because they do femininity better! Maybe knowing that someone is worried about the exact opposite thing you are, makes one realize how silly and arbitrary and in your own head the hang up is to begin with.

    I don’t know that anything ever feels natural, but you can at least recognize when you’re holding yourself back because of insecurity

    I find the comment about presentation getting easier or more natural as you get older to be funny, because a.) I assume the letter writer is like 40-50s based on the focus on butch/femme dynamics and b.) Style honestly got more difficult for me as I got older – less time and less money to shop for clothes, and spending less time in big packs of queer friends around my age whose look I can observe/emulate for experimentation purposes. Maybe I should get an Instagram purely for fashion help, hah! But honestly, letter writer’s sense of style feels as normal as their attractions – they’re not just attracted to butch/femme people, and they don’t want to dress like a stereotypical butch/femme person either. Well, makes sense. Those are kinda silly and forced categories, for most of us.

  6. As a bi woman hoping to enter the lesbian dating scene, I appreciate this advice. I rarely wear dresses nowadays because I find pants and shorts more physically-comfortable, and I’ve only ever worn makeup when performing in a play because it’s uncomfortable and I’m too visually-impaired to put it on myself. But my preferred personal aesthetic is otherwise more feminine, and I’d be inclined to emphasize that in my appearance when on a date (like any opportunity to ‘dress up.’) And I’m definitely more attracted to ‘feminine’ features, on women and sometimes on men. (My mother is also bi but has a strong preference for butches, so the women she thinks are “gorgeous” usually don’t appeal to me.) So I feel I don’t fit the stereotypical lesbian binary, and am glad to see indications that it’s now being treated as more fluid and less absolute.

  7. Soooo many people are masc4masc or femme4femme. Seeing that really set me free in terms of “Who do I want to be attractive to??” I just dress like garbage (with interesting glasses!!) and hope someone I’d be into is into it, without really expecting anyone to be or not be into me. If someone is it’s a neat surprise. BUT THEN getting attention from T4T peeps when I’m not trans has me wondering if they know something I don’t? like?? Queer dating’s really something.

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