Online Dating Blog

There are many mistakes that are made on first dates…far more than I will list here. However, I will cover the 10 mistakes that I saw from others while dating online, made myself while dating or have learned about by talking with other singles about online dating. If you are struggling to find second dates I would strongly recommend seriously reviewing this list.

1. Trying to Act Like Someone Else
Many people ask: How should I act on a first date? The truth is, you should not be acting. As a shy man I read a lot of advice that said I “just needed to be out-going or confident” and some of the advice even offered ways to give this impression. It was all a big show though. This is a problem for two reasons:

• If I fail, trying to be someone else did not even help
• If I succeed, I will have done so by convincing my date that I am someone that I am really not.

I discovered I could still be myself and as long as I was comfortable I still had great success. I realized that the advice that said I could not be myself was wrong. That said, shyness is only one area where we convince ourselves that being who we are is going to hurt our chances. It is true: it can hurt our chances…but only with the wrong people. There is nothing better than having success being yourself and when that happened for me I was so happy I was honest with myself and the women I met.

2. Believing That You Do Not Need to Prepare
The great thing about online dating is you have information that would normally be unavailable. Your date will reveal items through their profile and emails that you need to take advantage of. Many singles dating online believe that when they find that fairy tale connection, the conversation will naturally flow. They rely on the hope of chemistry to lead to a great first date. In my opinion this is a mistake. If there is chemistry, your knowledge and preparation will only help your chances on the first date. If there is no immediate chemistry you will be in the best position to ensure the conversations that night still goes well (and not every successful relationship has chemistry in the beginning!)

3. Lying in Your Dating Profile
I realize that lying in your profile may not seem like it qualifies as a first date mistake and in some ways it is not; it is a profile mistake. However, you will be paying for this mistake on your first date. This especially applies to lies on your appearance. If you say you are 3 inches taller or 10 years younger you will be revealed as a liar on each and every first date in the very first moment you meet. If the first thing your date thinks when they meet you is “they are not as tall/young/thin as they said they were” you may be finished before you even start.

4. Lacking Respect for Your Date
A lack of respect for your date is the keystone for many bad dating stories told today. A lack of respect is not just being rude to your date. A lack of respect can also be shown in how you pay for the meal or in how you dress for the first date or even being late for your date. Obviously, the ultimate lack of respect is standing your date up. I once had a woman stand me up because she was afraid of meeting someone from the internet but as you can imagine that excuse (which I believe was true) hardly repaired the damage. If you start yo suspect you are not going to be able to make it to your date for any reason, contact them and let them know! Had she called me and explained her worries I would have happily given her another chance when she felt more comfortable but being stood up was the end of her chances with me.

5. Bringing A Friend
For many just the idea of bringing a friend on a first date seems so strange that they laugh when they consider it. Still, this is advice that is offered by many people who have a primary concern of online dating safety. While I believe that safety should be a top concern there is a point where you can take things too far. I once had a woman bring a friend on a first date and I really tried to remain open-minded but the truth is we were never really given the opportunity to connect. At the end of the night I felt like I had not been on a date at all. If you are so concerned about the person you are going to meet that you feel you must bring a friend to remain safe, might I suggest you not meet them at all?

I do not see much point in meeting people when your chances are handicapped to the degree that this approach will create. I have many thoughts for safer online dating that do not require what I consider to be sacrifices to your success. You can find my thoughts listed here.

6. Sharing Too Much
I’ve covered this before but some singles take being honest way too far. You can be honest without revealing every detail about yourself. There are qualities that my wife accepted about me after we were dating but would have hurt my chances on our first date. This might be a subcategory of “being prepared” because you should know ahead of time what you feel most comfortable revealing. I disagree with the idea that certain topics will always be off limits on first dates. If you are using a dating site and discover you have shared religious or political beliefs then these are fine on a first date. Still, what you are willing to discuss is something you should decide ahead of time. Leaving a little mystery is actually a great thing to do!

There are many reasons a person might control the conversation and many times it isn’t intentional. Sometimes simple excitement over a good date causes us to make bad decisions about how much we are talking. Other times we can take our desire to be prepared for a date too far and end up aggressively interviewing our dates. Be aware of how the conversations are starting and how they are flowing so that you can be aware if you are being too controlling or too talkative. If you realize you are not being considerate with sharing the conversation, often the solution is as simple as remaining quiet for a few seconds. You may find your date has been anxiously waiting for a chance to get in on the conversation. For more see my post on remembering to share the conversation.

8. Texting
Every year we become more and more comfortable with our mobile phones. Many of us are comfortable to pull out our phone to start texting in the middle of conversations in almost any situation. This is a bad habit in all social interactions but on a first date it can be a killer. Every time you text you will be reminding your date that they do not have your full attention. It does not matter if you want to give them this impression or not: they are going to be hearing it loud and clear. For any of the “old timers” like myself who still actually speak into their phone to communicate, that’s a mistake as well on a first date. Put the phone away for an hour or two!

9. Discussing the Ex
Do not do this. Most of the time when I had a date do this, it was pretty obvious that the woman was trying to (in a round-about way) show me that she was worth going crazy for. There would be wild stories of the ex and she would always be somehow stuck in the situation where a man simply could not live without her. There are other reasons that people will find to discuss their ex, maybe just to complain, maybe because they can’t think of anything else to talk about. Obviously still bad ideas and this is a topic you should not be bringing up.

10. Getting Too Extreme
Getting extreme is often created by the overwhelming desire to be liked. Getting extreme includes things such as agreeing with everything your date says, being too aggressive with your pursuit of them or even being too reserved as you interact during the date. This can be difficult to overcome depending on your personality but it is something you should try to be conscious of as you interact with other singles. My opinion is that the more you date, the more comfortable you will become and the more true you can be to who you really are.