September 29, 2020

3 Simple Steps to Take it from a Wink to a Date

by Janet Tingwald in Dating, Internet Dating

Do you ever start to feel anxiety when you’re on an online dating site? Do you wonder, “Do I start the conversation or wait? What do I say when he responds? What if he starts to talk about sex?”

I want to share 3 simple steps with you so you can confidently navigate conversations online and either move things towards meeting or move on. (Because no matter how fun online chatting is, nothing is real until you meet.)

1. Always start with mindset.

You will get what you focus on. Monique, a former client of mine, came to me because she could not meet a nice guy. Now Monique is what you would call a high-quality woman but she did not attract high-quality men.

One day on a coaching call, after identifying her blocks, she was back on dating sites. Monique said to me, “I don’t know where all of these great guys came from, but I never noticed them before.” Your brain will only see what you expect to see.

2. Send a playful wink.

Now that you’ve gotten their attention with your fabulous profile, there’s nothing wrong with a playful wink on someone’s profile that catches your interest. At the most a question about something interesting that caught your eye. Past that, let them lead the engagement.

In this step, there is 1 main thing to achieve…narrow the field. You could think of this as screening applicants.

Take this time to find out if someone meets your requirements. (Because, if just one doesn’t fit, the relationship won’t work.) See how they respond to requests and boundaries. There are a lot of nice guys online, but many are bad daters. They’re using the same skills they used in college. Unless they go too far, give them a little grace the first time and ask for something different. If someone is sexualizing things a lot, tell him that you’re not comfortable with that kind of conversation, yet. Then see how he responds. Many times he will say, “Oh, okay.” If he doesn’t respect the request, you have your answer and can politely and quickly move on.

Ask questions relevant to what’s in their profiles or in their messages. Believe what they say.

3. Be honest, friendly and engaging in any and all communication. Keep messages light and a bit on the surface. Practice kindness with boundaries. Most of them are as nervous and unsure as you are.

When the communication starts to flow, in order to not get stuck in a perpetual texting loop, think in 2’s:

  • 2 messages,
  • 2 texts
  • 2 phone calls

The idea is to meet in person to see if there’s potential to take it further. It will also tell you something about them if they continue to make excuses and resist meeting. A simple, “Hey, what do you think about meeting Saturday morning for coffee?” will work. Remember, it’s paying attention to how they respond, and how that response makes you feel. (Hint: It should feel good.)

What to say? Well, there’s no way to give you exact words for every situation. Really, just be yourself; have a conversation as if you were at a party. Keep the conversation light, nothing too deep or too personal initially. Stay away from sexual innuendos, but a little banter or flirting is good. This is an opportunity to practice being yourself and practice boundaries. Your guy is looking for you and will like YOU just as you are!

Then meet in person or virtually. It’s not real until you meet.

For the next week, I encourage you to engage men in conversation for practice. You don’t have to meet them, but it will help you to relax and engage with men you are interested in meeting. I’d love to hear how it goes. Email me and let me know.

Bonus Tip!

Men usually DO NOT get as much out of online conversations as we do. They may get excited about meeting you and make comments, but don’t expect that they have gotten the same warm fuzzy feeling that you may have.


You can catch these tips and more from my Facebook Live (broadcast on September 23),