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Awkward First Date.

By Guest · Jan. 22, 2018 · Dating

A guy holding a bunch of flowers facing a street.

Have you ever experienced an awkward moment with someone that you actually wish you weren’t there? One of my young clients wanted to share this blog with you. When I read it I laughed out loud because oh boy do I remember moments like this. I am nearly 50 and I can distinctly remember all the uncomfortable people I have met along the way. I think that’s why I talk so much……. To fill in the gaps when there are these silences that make you want to curl up and die. My advice to you is be yourself no matter if you are the shy guy or the noisy girl …. BE YOURSELF. This allows you to not be even more awkward trying to be someone you aren’t.


First dates are awkward. They are times where knowing what to say is important.

I went on a date with a girl recently. I am someone who does not enjoy walking around shopping malls, but my date said that she wanted to go out to a restaurant for a couple of drinks with me and she suggested a shopping mall. So I decided to be polite and say yes to going to a place I normally hate. Don’t ask me why.

I am not a very talkative person when you first meet me; I prefer getting to know someone before I feel comfortable talking their ear off.

I am a sporty person who would like going on a hike or doing something where you don’t just walk around a shopping mall looking at stuff that you won’t even buy on a date. Now this date I went on had to be the most AWKWARD date I have ever been on in my life.

I spoke the entire time and she hardly spoke. I think she said a maximum of 10 words while we were out, bear in mind we went out for like 5 hours. I decided to write this blog for people like me, who don’t talk much when they first meet people or people who have no idea what to talk about on a first date.

So here are some topics and questions that might help you get a conversation started with someone you don’t know:

Talk about what they like doing, their hobbies. Are they into any sport, or do they prefer being at home with a good book or watching TV? If they like sports talk about what sport they like and why, or if they prefer books or watching things on TV then ask them about the book or what their favourite movie or TV series is and why.

Ask about what their plans for the future are. Ask where they see themselves in like 5 – 10 years. What goals have they set themselves?

Ask about places they have travelled to. Do they like travelling? Ask them where their favourite place to be is, or where they would like to go and why.

Ask things like who their biggest influence is.

What music are they into and who is their favourite singer/ band at the moment?

Do they have any pet peeves?

Do they have a nickname? What is the story behind having that nickname?

Here is some advice: If you are someone who doesn’t talk much when you first meet someone then DO NOT go out with someone who is introverted and shy, it will honestly be the most boring and awkward date you will ever go on, trust me when I say that. I wish I knew this before I went out with that girl. Oh and make sure you choose to go out somewhere that you both will enjoy.