My First Online Dating Experience: Not What I Expected

A few years ago, I had given up on the bar scene. The women I met only looked good in the dark after a few beers, or her personality was so bad it didn’t matter how good she looked. I knew it was time to move on to online dating. To be honest, I really didn’t have high hopes for when I signed up for Match.com – the first dating site I tried out. I just wanted to meet some women and see where things go. If the women I met were better than the ones I met in bars, I would have considered the experience a success.


I got signed up for Match.com, created a decent profile, started searching for women, and then contacted the ones I thought were attractive and shared common interests. I’m really not that picky of a guy. I just want a woman that is decent looking, has her act together, and has at least some things in common with me. I don’t think that’s asking too much.

Before I began emailing women, I got some pointers from a friend on how to send catchy emails and create an attractive profile. I’ve always been pretty good at talking to women, so I knew once I caught their attention online, I could work my charm. But I really didn’t understand how to actually get the attention of women online. It’s not the same thing as approaching a woman in a bar. So I was grateful for the advice I received.

My First Online Dating

My First Online Dating

Apparently my friend was an expert in online dating. Right off the bat, I began talking to an interesting, attractive woman. We spent probably 2 hours chatting on Instant Messenger before exchanging phone numbers and talking on the phone well into the wee hours of the night. It was a great conversation and she seemed very cool. I never would have expected to meet someone right away, but we decided to go out to dinner the next day.

Although it’s going to seem like I’m a pessimist, I really am not. I still wasn’t too overly enthusiastic and optimistic. Sure, she seemed great online and over the phone. And her pictures were nice. But I was still expecting her to look completely different and have a horrible personality. I’ve heard some really bad stories about online dating encounters.

 Online dating encounters

Online dating encounters

I put on my best outfit, slapped on a little cologne, and got a nice haircut. I was ready to impress. But since I still had doubts about how the date would go, I gave my buddy a heads-up to come bail me out in the event the date sucks. I let him know that if I sent him a text message during the evening to call me up and come up with some excuse why I must leave.

I never sent him a text message that evening. The date went far better than I could have ever expected. She didn’t look exactly like she did online – she looked even better. And, best of all, she had an even more fun personality in person than she did online and over the phone. I had a great time. I put on a good show for her too. I won’t tell you how the night ended. That’s between me and her. But I will tell you there were many more awesome dates. My first online dating experience went far better than expected.

Attractive woman

Attractive woman