3 Types of Dates You Might Have When You are Online Dating

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You’ve taken the plunge and tried online dating, you’ve found someone you’re interested in and can carry on a conversation with, and now you’re facing the prospect of meeting face-to-face. I’ve been on three dates now, all three with people I thought I was extremely compatible with based on our online conversations.

But the cliche phrase that you can’t judge a book by its cover is sometimes very true—and other times not at all! Here’s what I learned from my in-person, online dating experiences:

1. The awkward date

This was the first date I went on. He drove a few hours and met me at a coffee shop in my town. We had a very pleasant conversation. As we continued talking, I realized we shared many of the same opinions about various topics.

The date ended up being  pretty awkward, though. It wasn’t that we didn’t get along, it was that our personalities didn’t mesh in a romantic way. He is an introvert, I am an extrovert. I had more experience dating, he had had only one other girlfriend before. I felt like we were in different stages of life. I knew it would not work out between us, so I ended things a few days later.

2.The job interview

My second date felt more like I was interviewing for a job. When I arrived he shook my hand—which I’m sure is fine for some, but I’m a hugger! It felt too formal a greeting for someone he had already been talking with for a several weeks. But I shrugged it off and sat down. The conversation was great and we seemed to hit it off just fine. But it did not feel like a date. It seemed to me that he was keeping me at a safe distance, asking only safe questions, and treating me like he was interviewing me for a job.

It only lasted two hours, and he shook my hand again before saying goodbye. He ended things a few days later—not surprising given how unnatural the date felt.

If this happens to you, don’t let it get you down. Just as I knew it wouldn’t work with the first guy, the second guy knew we weren’t right for each other. You shouldn’t fault someone for doing what is right for him.

3.The one that made it all worth it!

With my third and final date, I’ll be honest, I was a little nervous. Not to meet him, but nervous that it wouldn’t work out. Because based on our conversations, I was especially interested in him. But after dates #1 and #2, I didn’t want to get my hopes up too much.

He drove an hour and a half to pick me up at my apartment. Only minutes after being around him I could tell how fun the evening was going to be. We went to my favorite coffee shop and found my favorite spot next to the window.

We talked for almost two hours. It was incredible how well we got along. We both had no problem making the other laugh, a few times he jokingly gave me a hard time about something. I couldn’t stop smiling; I felt like I had known this man for years. After leaving the coffee shop, we went to my favorite restaurant where I found myself actually excited about the 30-minute wait— because it meant we had more time to talk!

It’s no exaggeration when I say I don’t think I have had that much fun in a long, long time. There was no question by the end of the evening that we both wanted to go on a second date.


With online dating, you may think you know what you’re going to get when you meet someone in person, but the truth is that you never really do. Let me encourage you, though, to push through the awkward dates and the dates that feel like a job interview. When you go on the date that’s worth it, you’ll be thankful you did.

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