How to Strike Up A Meaningful Conversation with Someone of the Opposite Sex.

After coming out of an 8 year relationship, I realized I had no clue how to talk to women anymore… at least not now that they were potential girlfriends. The funny thing is, I never had an issue when I was married, but now being single, it felt like I had lost all social skills and had no clue what girls wanted to hear. At the beginning, I tried to impress women by talking about my job, money, cars… anything that I thought would make them fall head over heels for me because I had so much to offer. I quickly realized the exact opposite would happen! I could see the women I met become almost immediately disinterested, looking around for an escape from this terrible conversation with a guy that just wants to talk about himself. (Side note: if you have a hard time recognizing what people are thinking, how they are feeling, or what the “vibe” in the room is; look into increasing your “social awareness”. A concept that is brought up a lot in material about increasing your Emotional Intelligence.)


After coming to this realization, I started focusing on getting people to talk about themselves more. To be honest, I was clueless as to how to start up a good conversation with a women and it seemed like every time I did, it would die out after a few minutes. Without realizing what was happening, I was suffering from the “cloud” effect; a defense mechanism that happens when you get nervous or anxious, all the sudden you can’t think clearly and have no clue what to say. I’m sure you have experienced this at some point in your life, when you “freeze up” before talking to someone you envy or get “stage fright”. There is a lot of literature out there on the effects of “stage fright” with regard giving public presentations, but many of the same principles apply when nervously trying to hold a conversation with someone new.


Here is what I did (and what you can do) to conquer conversation with the opposite sex:

  1. Realize that material things matter very little when building emotional connections with people
  2. The more people share with you about themselves, the greater the connection they feel with you (again, has nothing to do with you!)
  3. Start out by going to a restaurant with a pretty waitress and try striking up a conversation with her (this is an ideal starting place since you already have to talk to her to put your order in)
  4. Ask her a simple question, something like, “How is your shift going?” or “I’ve never seen you here before, how long have you worked here?”
  5. Here is where most people get stuck! And here is a trick to help you get past it and stay focused on the conversation: listen to their response and find one word in their response that you can ask another question about! This shows that you are listening and that you care what they have to say.
  6. If you get stuck again, don’t panic, silence isn’t always a bad thing. Just wait a second, then repeat Step 5 (this probably goes without saying, but DON’T ask the same question again!)
  7. Practice, practice, practice. Just like anything else in life, conversation is a skill that can be learned, but it takes lots of practice!

Remember, you will stumble, fall and may even feel like a failure at times and that is okay. That is temporary. Every success you have had in life so far, whether it is at work or otherwise, took you a lot of hard work and dedication. I’m sure if you think about it, you can think of a time where you failed but got right back up and tried again. The more you do it, the more you learn from you’re mistakes and the less you will stumble and fall. Soon you’ll find that you have conquered the art of conversation and are living a much more fulfilling life!

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