Chatting With A Potential Date Online

Gay Dating

Chatting With a Potential Date Online

Jonathan Welford

Written by: Jonathan Welford

Jonathan Welford

Jonathan Welford is a dating and relationship coach, author of three relationship coaching books and regular columnist. He heads up a coaching and therapy practice specializing in dating and relationships. He lives in the UK with his husband and their English bulldog named Lola.

Edited by: Lillian Castro

Lillian Castro

Lillian Guevara-Castro brings more than 30 years of journalism experience to ensure DatingAdvice articles have been edited for overall clarity, accuracy, and reader engagement. She has worked at The Atlanta Journal and Constitution, The Gwinnett Daily News, and The Gainesville Sun covering lifestyle topics.

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You’ve picked an appropriate dating website to fit your needs and have the type of guy who hits your desired demographic as an ideal match. You’ve set up your profile, included an informative and fun summary of your goals, likes and dislikes, and sketched out an outline of your ideal guy. That wasn’t hard was it?

Actually, it takes time and trial and error to get something that fits, but spending the time to get it right is worth its weight in fantastic and inspiring dates and your possible life partner.

Only launch your profile when you think you’ve got it right, and have a friend check it out and give feedback on how it sounds before you launch it. You have only one time to make a good first impression.

With every new profile, you will be fresh meat to the guys on the site, and curiosity will bring a series of men to you like bees to the honey.

“Marvelous!” I hear your say. Yes, it is (but some may be less savory than others). This is the time when guys will be flinging you messages to say “Hello.”

But what do you say and do? Here are the top points to look at when interacting with guys online.

1. Rejection.

If you are completely turned off with a guy, don’t be rude. Just say, “Thank you for your message. Your comments are really appreciated, but I don’t think we’re a match.”

Don’t get into the whys or reasons. Leave it at that and save the energy for the guys you’re interested in.

2. Too enthusiastic.

You get a message from a guy overseas, declaring his undying love and attraction toward you. He thinks that just by reading your profile, you can have a life together and overcome the distance and the language barrier.

Stay clear of these types of men and refer to the brush-off comments in point one.

3. You don’t know what to say?

You feel frozen and stuck for dialogue. Don’t stress, this isn’t a bar chat-up where the need for a witty reply is needed immediately. You can go away, have a coffee, watch some TV, and then reply with your answer.

This is online life, not real time, so there’s no huge urgency. If they don’t reply again, don’t worry. It wasn’t to be and you can move on to the next one. There will be plenty of other men out there. It’s like shooting fish in a barrel.

These are men looking for a man, so keep the banter frothy and current and keep an eye out on recent news to discuss. Or talk about the weather or what’s happening in TV shows you both follow. Go down his profile list and get an idea of what he’s like.


“Online dating takes the immediate pressure

off approaching a guy in a social setting.”

4. Do not lie.

If you’ve posted pictures of you leaning against a Ferrari, don’t make out like it’s yours (unless it is). Also, don’t post pictures of you looking hot in your skimpy shorts when you were 20 and you’re now 20 years older and the same in pounds heavier.

You will be basing a relationship on an untruth, and ultimately, it will not end favorably.

5. Arrange something more.

After you’ve chatted for a few days, arrange to chat on the phone or meet up for a coffee. If the person is reluctant to do so, move on. If you wanted a pen pal, then you wouldn’t be going on a dating website.

6. Sharing pictures.

If you are looking for a casual hookup, then feel free to start flinging your favorite adult-rated pictures of yourself. However, if you’re looking for a relationship, save those pictures until you start to get intimate in person.

7. Chatting on webcam/Skype is fine within reason.

It’s a time when you can see your potential date in real time and hear how he sounds and talks. Some guys have sparkling wit and charm online and are as dull as ditch water in real life.

You want someone who directly correlates in real life to their online persona. Allow a small buffer of difference for nerves on the first meeting or chat. Avoid stripping off and showing each other your “meat and two veg” to the camera.

First, there are a few scammers out there where guys film the webcam output and post it on a variety of X-rated sites. This can have huge repercussions and be vastly embarrassing for you.

Be wary and be careful using this media. Avoid drinking alcohol and taking other substances when chatting online and using webcams.

8. Use open questions.

Start with “What, where, when, how or why?” Closed questions shut down the conversation and make things stilted.

Here are a few good opening questions to ask. “I’ve seen your profile and I see you are interested in travel. Where have you been recently?”

Offer a little information about yourself in each message, such as “I recently went to Paris. It was all that I expected and more.” If someone is interested in you, they will automatically ask, “What did you expect?”

Leave each message open to have questions asked about it, as this keeps the dialogue fresh, stimulating and interesting.

9. Dating may seem like a job interview.

In many ways, dating is like a job interview. However, let your personality come through. Being overly formal is a turn-off to some, as is seeking too much attention with outrageous comments.

Again, this is trial and error, so you will find your own balance in time. Don’t be worried because you can always hit the delete button.

10. Still meet new people.

This is online dating, not an excuse to hole yourself up on your own in your home, typing frantically away on your computer for months on end.

Online dating is a facility to meet people, not replace that activity with an online character that has more fun than you do, leaving you to live a solo life on your own. It’s a service and make sure you use it in the correct way.

Ultimately, online dating takes the immediate pressure off approaching a guy in a bar, at work or in a social setting. However, you will still have anxiety when meeting for the first time, but at least you have established a common ground of interests.

The dating starts from the first meeting, which is why it’s important to meet earlier rather than later, as the longer you chat online, the more pressure there is to turn it into a physical relationship at an earlier stage than you originally wanted.

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