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How to ask your transgender crush on a date

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As a former sex-worker and a transgender woman, I can get a little neurotic… well, paranoid, every time a guy asks me out on a date.  I always have the feeling of being only wanted for one thing and it usually includes a mattress… or a floor! Who knows what you’re into?  Alright, Jacob, I’m not saying that I’m a prototype transgender woman when it comes to dating but I am a person with experiences and you may be able to get some key information from me and you’ll never know how much in common your crush and I have.

Let’s begin with the most vital part that can make or break your dream with your future transgender date


They say that first impressions do not last but you have to remember that when it comes to dating, nothing will last when it begins with absolutely nothing.  Don’t risk your “maybe only chance” in going out with your crush.  I don’t think chivalry will ever go out of style so be polite when you ask your crush out but not too polite that will make her feel like you came straight out of the 1800s.  Some of us like swag too so try to stay in the middle of the gentleman and bad boy area.  You can start by writing the following via a message through your favorite transgender dating website:

  1. I’ve been having lovely conversations with you and I’m just wondering if I can take you out on a date on *insert date here* (concise, sweet, and respectful. I’m pretty sure you won’t get a no)
  2. Lately, I’ve been thinking about meeting you in person because I find that you’re an interesting and lovely (yes, abuse this word) woman, would you mind going out on a date with me?
  3. You’re a cool and lovely (yet again) gal, I’d love to grab a bite with you sometime. How about this *insert day here*?

If your transgender date rejects you with a reason involving a conflict of schedule, you can ask her if she’s available on another date.  However, if she gives out seedy reasons as to why she can’t go out on a date with you, she’s just not that into you and you must acknowledge that fact and move on.  Date me instead, just kidding.

Date Night

There’s nothing wrong about day dates but there’s something about the atmosphere at night that magnifies a romantic ambiance.  I’ve written about ideas on where to take your transgender date on the My Transsexual Date blog if you’re so inclined.  Be sure that your date will be well-thought-out and not just on a whim.  Consider dating as an investment, low risks, low return.  Make it magical!

Pay for the Bill!

Sweet Jesus Christ, if you won’t be able to foot the bill on the first date, don’t think about dating anymore.  Unless she’s persistent about paying it (I split the bill in half if I don’t like the guy), your wallet must be always open to the consequences.  Don’t take her to a place that you can’t afford.

Good luck sweetie!



Posted in Love and Relationship

About the author

Amanda Valentine Dela Cruz
Just a random trans woman playing with makeup and skincare. Loves bacon and the operating table. I'm also the author of the dating guide book Dating Transgender Women for Gentlemen. Know more ->

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