I commented tonight on a wonderful post by SugarCunt, Online Dating Mistakes and 5 Steps to Avoid Them (which you should totally read by the way). My comment amounted to a post in itself, so I reproduced it here with some slight alterations.
1. Telling a Complete Stranger They are Attractive: A Primer
Most women who are beautiful in the conventionally-attractive sense already know this, because they receive comments and cat-calls all the time. Telling a conventionally-attractive woman she’s beautiful as a pickup line is like saying, “Hey girl, you’re five-foot-six and wearing a blue jacket.” Yes, this is a factual statement that is quite apparent. Nobody is impressed by pointing out the obvious.
If you want to compliment someone on their appearance, mention specifics. “Your hair is so gorgeous.” “You have a wonderfully intense look in your eyes in that photo.” “That is an amazing hat.” A generic “you’re beautiful” shows that you aren’t paying attention to the person. It’s the visual equivalent of messaging someone without reading their profile. It is a statement spoken at a person instead of with a person.
If you’re messaging someone who isn’t conventionally attractive, this is even more true. People who don’t fall under conventional beauty norms also know this fact, because they often receive either a) negative comments or b) are completely ignored/dismissed. A blanket “you’re beautiful” in this case will come across as dishonest and manipulative. As if you think they’re so desperate for approval they’ll take whatever they can get.
Specific compliments show you see the person, not just their body, and that you have put thought into why they interest you beyond causing bloodflow to your groin.
2. How Not to Message a Person, Especially Not a Trans Person
The following are real quotes from messages I have received through online dating sites.
“Question… Are you transgendered? Not sure what the last part of your profile meant.”
This was the entire content of the message. It was sent by a couple seeking a third for flings. There are several problems I see here:
1. Writing a message this short asking only about someone’s trans status shows that you’re curious, and curious in a bad way. The zoo exhibit “why are those monkeys doing that” kind of way. Trans people get this a lot. Don’t do it.
2. It is pretty obvious in this particular situation—given how most straight-couples-seeking-thirds are—that if the answer to this question is “yes”, the trans person will be rejected. This means you are setting someone up for rejection by revealing a basic fact about themselves. This is insulting, especially when their trans status is mentioned in their profile. It’s clear you suspect the person is trans, and that this is somehow a complicating factor that must be sorted out, so what you’re really asking is “Are you unfuckable?” Not a great opener.
3. Saying “transgendered” is generally considered a faux pas. It’s a red flag to a large number of trans people that you don’t know anything about us. If you are interested in dating a trans person, don’t use that word, even if later you discover the individual in question might be ok with it. The safest word to use is “transgender” or simply “trans”. It’s an adjective, and it describes a person. It’s not a noun or a verb. And it should never be the first and only question to a potential partner.
“I kept reading your profile. I got up the guts to write. I would love to know you better. I know you must get a ton of replies so I will keep this brief. Please look over my profile and let me know what you think.”
The flubs here are less severe so I’ll be gentler. This message is very sweet but also a bit desperate-sounding, like I’m being put up on a pedestal. Most people don’t enjoy that, especially not women. The last bit sounds like I’m being asked to look at a resume. There are also no specifics; you could send this message to literally anybody.
“very intrigued by your profile, sexy and reference to firefly!”
I’m going to be honest, I’m more tolerant of being objectified and called “sexy” when it’s coming from another woman. But yeah. Single-sentence. Single sentence messages don’t give a good first impression.
“Thanks, but not interested! I’ll check out that book though, thanks for the recommendation.”
This was in reply to a message that was not a proposition, but in fact a strictly platonic book recommendation based on the person’s profile. A person who listed they were also looking for friends. If you’re also looking for friends on your profile, don’t assume every message is a come-on.
“You had me at video games and sub play 😉 Hello darlin, open minded, down to earth, definitely not normal guy looking for the untraditional kind of gal for randomness and friendship, swap stories and see where things may take us.”
NEVER EVER CALL A TRANS WOMAN AN “UNTRADITIONAL KIND OF GAL”. It makes you a traditional asshole.
I received one message from a couple who said they were open to dating “tgirls”, but only “passable full time Tgurls.” This language not only makes you look like an anachronistic relic from the 80’s, it’s also a one-way ticket to block-ville.
Now it’s time for the LIGHTNING ROUND!
Subject: “Wink” Text: “hello there”
…Are you serious?
“Tell me more!!!”
“A wink…and a smile :)”
An anxious look and a few steps in the other direction.
“heya hows it goin? you seem like a fun girl. lets connect”
This is a missed connection.
“I seen you on facebook. I am the infamous [name withheld]”
“new friend would be fun let me know”
From a profile with a sexually-suggestive name and no photo. AXE MURDERER ALERT.
“Can I txt you..”
After you’ve proven you’re not an axe murderer.
“hello soo what type of coffee do u like”
Solitary coffee, at this rate.
Subject: “girl” Text: “well i hope so.”
Dying in a fire. Well I hope so.
“you go girl rock out”
For those who don’t know, “You go girl” is code for “I find your transness quaint and amusing.”
I’ll close with something positive: I had to dig through a lot of messages from wonderful people whom I just didn’t share any chemistry with to find these. Online dating isn’t always a trip to hell, but sometimes it’s a scenic tour.