Step-by-Step Online Dating Tips for Men

After a few years of online dating, I’m beginning to see patterns in the process. The men who score dates with me seem to know what they’re doing from the first message to the first date because there are steps that make a woman feel comfortable and build just enough anticipation but not too much expectation.

Steps from First Message to First Date

Write a First Message. I recently met a man who said he only receives around one or two replies for every thirty messages he sends. Ouch. BUT… that doesn’t deter him from reading through a woman’s entire profile and any questions/videos she may have. Why bother wasting your time or hers? He will then carefully craft a short but specific message that taps into who she is. Trans women are unique so make your message unique! I told him I only get one of these “personal” messages in about fifty… and that these are the ones I reply to. The rest are just informal “Hey, how are you?” types which say to me: you are bored and boring!

Switch to Texting. Once there are a couple of back-and-forth messages on the site, you may want to give her your phone number, especially if you know you won’t see each other right away because of scheduling differences or whatever. This shows her you are very interested. It’s also nice to be able to communicate “off-site” rather than having to log in every time you want to chat. (If she isn’t comfortable with exchanging her number, then be completely respectful and continue to communicate online until you do meet.

Be Playful and Flirty. When I first got a cell phone, I remember my friend saying, “You don’t understand how to text.” I scoffed at her criticism but now see there is a finesse to be had, especially when it comes to dating. Use these predate texts (or messages) to get to know her a little better, without being too intrusive. Communicating with a trans woman requires more restraint because you don’t want to come across as intrusive. Never get sexual unless she does first, and avoid those impersonal “Hi. How was your day?” kind of questions. Ask about her interests, what you’ve read in her profile. And sending cute photos are also fun.

Try a Sound Check. Yep, I’m talking about actually calling her. I know, no one makes phone calls anymore, BUT they should. And if she’s a little older like myself, she’ll really appreciate that gesture. There’s something nice about hearing someone’s voice before meeting them. You may be surprised by the sound of her voice, but she won’t see that look on your face. I recommend a quick text beforehand, just to say, “Can I give you a call, are you free?” so you don’t take her by surprise and make her feel anxious. This can also be a great time to bring up meeting in person.

Here are some great first date ideas and tips on how to impress your trans date.

Tell us what you think

Notify of
Inline Feedbacks
View all comments