How to Date a Trans Woman

Eva Sless Eva Sless on 19 September 2020    35 comments
Beautiful dark skinned trans woman wearing a black dress and making a heart shape with her hands

This topic was one we have received a few different questions about, both from men wanting to date trans women, and from trans women wanting to help clear some of the myths and misconceptions surrounding trans women and dating, and, to be blunt, educate y’all on how not to be offensive or rude in your pursuits.

As most of you are aware, I am not trans and so in writing this piece I spoke to a number of different trans women to get their perspectives and advice, and I bring you the following piece in their words.

We Are Women

“One thing that really needs to be said first and foremost is that trans women are women. They are not ‘men in dresses’, or ‘men trying to trick men into sleeping with them’. If this is the sort of thing you are looking for then you need to find a cross-dresser or similar, not a trans woman. It’s usually pretty clear on a dating profile which one they are.” - Penny
“Approaching a trans woman for a date is the same as approaching a cis woman for a date. ‘Hi, would you like to go on a date?’ It’s not rocket science” - Kate
“You are not gay!! We present as female, consider ourselves female, and want what females want.” - Alice

Don’t Keep Me A Secret

“I’ll know you’re serious about dating me when you introduce me to your best friend. In my entire dating life I have met only 2 best friends, and not a single parent.” - Penny
“I don’t expect you to shout from the rooftops that you’re dating a trans woman, but if you can’t tell your friends, then I don’t want to date you.” - Helena
“We get enormous interest. I can get [up to] 300 messages a week from guys and girls. It can be overwhelming! But even the few that actually want to date won’t introduce you to their circle” - Alice
“I’m not going to be your dirty little secret. You need to be as proud of dating me as you would be dating anyone. I will take celebration or I will take nothing!” - Kate

Respect Goes A Long Way

“Don’t ask me about my genitals. It’s gross. If you want to date genitals then don’t date me. I am far more than what’s between my legs, and if you want to get between my legs you’ll understand and respect that” - Kate
“One way to tell [if someone is respectful or not] is that they are prepared to meet you in a public setting such as a cafe, bar, or restaurant etc.” - Alice
“Don’t tell me I ‘pass’ as a woman. That’s pretty fucking rude and just shows me you don’t think of me as a real woman. Which I am.” - Penny

We Are Not Your Experiment

“I once had a guy tell me he wanted to go out with me because he was thinking he was bi and wanted to check. He couldn’t understand why I got offended at that. Let me break it down for you. I am a woman. You are dating a woman. You are only bi if you are also dating a man. I am not a man. Therefore you are not bi” - Penny
“I get it. We are a bit different and a bit of a novelty to mainstream cis-ers. But we actually aren’t your ‘novelty toy’. We are humans. There are people you can pay if you want to ‘experiment’, but my life and heart are not there for you to play with and satisfy some fetish urge” - Helena

Forget Porn 

“Please don’t use ‘porny’ terms to describe me. I am not a ‘lady boy’ or a ‘chick with a dick’ or a ‘tranny’. If you are really interested in [dating trans women] then you also need to understand what words and phrases we don’t like. [Porn] is probably the worst place to get your information on us. - Kate 
“Guys want to meet because they think we will ‘top them’, or come to our place just for sex, or they [think of us as] free sex workers because they [associate us] with Thailand.” - Alice
“I am not a fetish. I am a person. Want to play fetish? Pay someone.” - Penny

Fight For My Rights

“Call out transphobia wherever you hear it. I don’t care if it’s your dad. You want to be my partner, then you fight for me and defend my honour like you would any girl.” - Helena
“I need to be able to rely on you for safety and comfort. [Things can be] really hard and dangerous out there for trans people. I need to know you’re on my side.” - Kate
“Fighting for the rights of trans people is also fighting for the rights of cis people to date trans people without all the bullshit. So when you fight for me, you’re also fighting for yourself” - Penny

Take Me Out

“Movies are good. Restaurants too. Love a good museum. Basically take me out to cool places and don’t hide me. Yes, sure, cooking dinner for me at home is really nice and sweet and romantic… [But if it’s] every single time we ‘go out’ then I’m going to get paranoid you don’t want to be seen with me in public and that’s bullshit.” - Helena
“Show me off! Take me out! I am your date and I want you to want the world to know it!” - Kate
“[The good guys] are happy to do anything with you that any guy would with his girlfriend, but that shit is rare as rocking-horse poo. My main aim is to help people move from the closet to the mainstream [and to] highlight that it is okay to date trans people and your friends won’t ridicule you. More likely they’ll be jealous!” - Alice

It’s pretty straightforward really. Treat people like you want to be treated with respect, kindness, and  compassion. While yes, there are a whole lot of factors that come into play when dating a trans person, and a lot of re-learning and understanding you might need to educate yourself on, finding love and companionship with that special person is absolutely worth the work. Just like in any relationship with anyone of any gender. And to all our trans sisters and brothers who are here looking for love, we wish you good luck, good fun, and most importantly, good loving.

Trans women can join Adult Match Maker and register as Female. We don’t force them, or trans men, to choose Non-binary although that option is available to those who prefer it. We don’t discriminate and also expect our members to show the same understanding and respect. Reporting trans members for not registering as Non-binary will be ignored as they are not breaking site rules. If you enjoyed this article, check out Eva’s earlier post 7 Things Transgender People are Sick of Hearing

Read Next Article

Likes & Comments

Comments (35)

  • JeanMichele

    JeanMichele
    Account closed

    Wow
    >4w
    Reply
  • logical01

    logical01
    Account closed

    Very good article, respect a person for whom they are, not any preconceived ideas or believes you may have, be they a hangover from the past. A woman is a woman so treat her as such, if you can't walk her into a restaurant, a movie or a party with your friends or family then it's you that has the problem, not her, if she's good enough to want, be proud enough to show her off..
    >4w
    Reply
  • SSExplorer

    SSExplorer
    51M 39F Newcastle, NSW,
     AU

    That is a very good article. I find I am attracted to trans women as they are usually close to what my mind feels is beautiful in a woman. As a couple we would adore to have a mff relationship with a trans woman as much as a cis woman. Our stumbling block is that with either we need privacy as being a family couple society isn’t ready to accept couples dating others just yet. I can see this being construed that we are hiding because of being trans. If I was a single guy I would have no issue with dating a trans woman just the same as a cis woman and would love walking down the street with my arm wrapped around the hottest girl in town :)
    >4w
    Reply
  • Latelygirl

    Latelygirl
    Account closed

    Congratulations Eva on a fantastic feature on ‘trans respect’. If your contributors Penny and Alice are who I think they might be I know both of them to be very wonderful women. Before lockdown I would see Penny and our other trans friends at social gatherings. I cant thank them or you enough for this very important expose. Best wishes
    Fran ‘latelygirl’
    >4w
    Reply
  • BBWmature

    BBWmature
    Account closed

    Great article....we all just want to be treated with respect! I can relate to some of these issues...I’m a big girl & find lots of men want to fuck me but rarely would any of them be seen in public with me! Good luck girls...it ain’t easy out there!
    >4w
    • MessyKnickers

      MessyKnickers
      Account closed

      I'm bbw and I was having the same thoughts reading their comments about guys not dating in public.
      >4w
    • MsShazza94

      MsShazza94
      55F NSW,
       AU

      Yes BBW lovers often keep the bigger girl at home for sex but don't take her out. I avoid guys who talk about being chubby chasers or BBW lovers.
      Love me not my fat bits
      >4w
    • LegsLicious
      Online status icon

      LegsLicious
      47F QLD,
       AU

      Gish I'm a size 10 and all I get are guys hitting on me in public, on a bus, at a bust stop, on a train, ferry, night club, restaurant.
      Femme Invisibility is Real. Wish girls would hit on me.
      >4w
    • RandyMandy73

      RandyMandy73
      Account closed

      I would not sleep with anyone that refers to me as a ‘ BBW ‘ period. You aren’t about to meet men that want to date you on here, you are on the wrong site if you think that’s what you’ll find. I’ve been married and another long term relationship. I meet men easily, I’ve always carried weight. Not every man I meet I would date, you have to be selective. If you are desperate, they’ll sense that a mile away. Respect yourself enough to wait for someone worthy of your time and energy :) sex is sex, dating someone that moves you on all le ems is another ball game entirely.
      >4w
    • BBWmature

      BBWmature
      Account closed

      Have never thought I’d meet Mr Right on here, I’m just here for fun! It was a general statement sympathetic to the article & transgenders being judged!
      >4w
    Reply
  • bambilovebris

    bambilovebris
    Account closed

    a nice blunt informative piece. as trans women we all have differing experiences and expectations. However they may vary they revolve around all those topics. it is very simple in reality, my gender is not my sexuality these are 2 very distinctly different topics.
    >4w
    Reply
  • Hillshornyduo

    Hillshornyduo
    54M 51F Parramatta, NSW,
     AU

    Great article :)
    >4w
    Reply
  • Tosca99

    Tosca99
    Account closed

    Beautifully written. Just imagine one day not needing to have to write such an article. We are who we are.
    >4w
    Reply
  • itsourtime

    itsourtime
    65NB 61F SA,
     AU

    Lovely written article makes you understand more about who we are and can be in a honest world .. I’m so lucky to have a partner who encourages me and my love to express my love to be feminine...
    >4w
    Reply
  • Transtastic16

    Transtastic16
    Account closed

    All good advice. It's pretty obvious to me day in and day out that no guy reads this!
    >4w
    Reply
  • SeafordTrans76

    SeafordTrans76
    Account closed

    Thankyou,thankyou, for once I didnt have to say much here, relief at last.great author.!!
    >4w
    Reply
  • MasculineFtM

    MasculineFtM
    43T Unley, SA,
     AU

    Great read, Eva. Thank you for including *trans folk as one of your article topics. If you intend on doing one on trans men in any regard, you're more than welcome to contact me for any information or help. Keep up the good work AMM authors!
    >4w
    Reply
  • Recudes43

    Recudes43
    Account closed

    Loved loved this article and presenting the viewpoint of trans people in such a candid way. I think the way one treats a trans person speaks a lot about a person's maturity.
    Having a coffee or drink or going to an event with a trans person should be no different from doing the same with a cis person.
    Men, you will get looks from people, that's the sad state of the society we dwell in. But are you "man" enough to grant your partner the respect and dignity she deserves.
    >4w
    Reply
  • Alicewho

    Alicewho
    55M2F NSW,
     AU

    thank you so much for sharing some of our concerns, I truly hope guys will read it and take notice. I know I told a few guys that the message wasn't sinking into about the up coming article and they have read it and went ...oh shit ... " i need to rethink my approach" once again thank you for putting our experiences out there
    >4w
    Reply
  • katelee63

    katelee63
    63F NSW,
     AU

    Transwoo
    Hi I am post op Trans and honestly I am proud of making my change. After reading this article it has opened my eyes to the pain we girls feel with the (opposite) sex ha ha!
    I have kept my transition a closely guarded secret after being abused for just having my ears pierced,
    go figure!.
    I am honestly in love with my new life,
    Unfortunately I had spent faaaaar to my time in my old shoes!
    I really enjoyed reading your article it just made me feel so much better knowing that other people are feeling the same way and have the same expectations
    >4w
    Reply
  • letsplaynow66

    letsplaynow66
    44M VIC,
     AU

    I love Trans women and I find it hard to find them I wish I could find trans for fwb.
    >4w
    Reply
  • Casualbiguy

    Casualbiguy
    44M Faulconbridge, NSW,
     AU

    Great article, and hugely informative. As a pansexual guy I’m ashamed to admit that I’ve fallen into one or two of these mistakes in the past. I have great respect and admiration for the bravery and honesty of all trans people, so I pledge to do better in the future
    >4w
    Reply
  • LegsLicious
    Online status icon

    LegsLicious
    47F QLD,
     AU

    You'd be stunned how many AMM male and female members call me a Tranny, or Chick with a Dick, or a bloke, or a man in a dress.
    I even have, unfortunately, a brief description of why I'm not trans in my profile.
    I'm not Trans. Transwoman don't have periods. Telling me I am is abuse. The same abuse that I endured as a Child, which ironically as many on AMM are parents would hate their child to experience.
    Thankfully there are some men who are nice.
    Unfortunately, I'm Lesbian, so finding women is as Impossibly difficult for me as it is for a male finding a woman.
    And women thave told me they are intimidated by me because I'm attractive, intelligent, talented, confident, and carry myself well.
    Isn't that why every woman wants?
    >4w
    Reply
  • LegsLicious
    Online status icon

    LegsLicious
    47F QLD,
     AU

    Oh and God ibhate it when people tell me I'm brave. Brave for doing what? I discovered the parental lie about my body 14 years ago. When "Transgender" wasn't even a social term outside a few males watching porn secretly.
    What's brave, is a transwoman who tolerates people telling her she's brave.
    >4w
    Reply
  • Annandalesparky

    Annandalesparky
    52M NSW,
     AU

    Great article!
    As usual, well written and informative.
    >4w
    Reply
  • TheRealDeal73

    TheRealDeal73
    Account closed

    Interesting, but one thing that sticks out is a comment that was made, it said that trans women are women they think of themselves as women which is great, but get up set that they arent introduced as a trans woman,. If you think your a woman than why get pissed cos the guy introduced you as a woman instead of trans woman. To that's a little hypocritical. You can't have it both ways
    >4w
    Reply
  • Desirable4u

    Desirable4u
    Account closed

    thank you Eva ox
    >4w
    Reply
  • Photos in private gallery

    hornycpl333
    43F 43M Melbourne, VIC,
     AU

    Great article! Trans women are the best!
    >4w
    Reply
  • MilkyMilo

    MilkyMilo
    Account closed

    Great article!
    I’ve dated trans girls in the past and, luckily, I was mature enough to have abided by these points.
    Fighting for trans rights is an interesting point and very valid if you intend on genuinely dating trans women. Noted!
    >4w
    Reply
  • princesskitycat

    princesskitycat
    48T VIC,
     AU

    I really cringe when cis folks write about a transwoman of experience but this article isn’t written by Eva it’s her asking questions from transwoman and then her final thoughts, so i like this article.
    Part of the blame of transwoman dating men in secret is to do with us by allowing this happen.
    But in past 15 years men’s attitudes towards transwomen in Australia have shifted a tiny bit.
    And partially because we have all said enough is enough, either take me as I am or you have nothing. And that’s because a lot of us have taught and educated eachother and our young ones to only be involved with guys who are proud to be with you and not be ashamed of you.
    There are so many men now who don’t care and aren’t ashamed they love us and are proud of us.
    Men on AMM is a whole different story, yes they want to be private and guess what so do I, that’s why I’m on here lol..
    My gender is not a dirty secret.
    >4w
    Reply
  • SeafordTrans76

    SeafordTrans76
    Account closed

    This is an interest piece,probably the best article I've read online in some time.Its written to inform in a candid way that modern journalism lacks,due to the politicised slant they often sell out for,that and capitalism.Being a trans advocate or championing any ideal is a mature minded pursuit,may as well stand for something as opposed to being a total sell-out like our current government that stand for nothing good or positive.Under them Australia never benefits,but their pocket books do.which is worse a minority that exists you've never met,that has no proof of malice and that only seek to live like everyone else vs an elite few,who live off the taxes,above the law,commit heinous Acts of criminality,corruption,sex crimes and escape justice at every turn,even changing our once proud democracy..that's a rhetorical question.but your choice matters in life if you believe you'll be judged inevitably in your final demise.
    >4w
    Reply
Copyright © 2025 Eva Sless It is illegal to use any or all of this article without the expressed, written permission from Adult Match Maker and the author. If you wish to use it you must publish the article in its entirety and include the original author, plus links, so that it is clear where the content originated. Failure to do so will result in legal action being taken.
The content posted on this blog is intended for informational purposes only and the opinions or views within each article are not intended to replace professional advice. If you require professional relationship or sexual health advice you should consult with an appropriately trained and qualified specialist.