Three Tips That Will Keep Your First Dates From Being Boring

More often than not, when my friends and clients give a recap of their first dates, the first thing they say as to why it was bad one is because the person was “boring”. They were self absorbed. They didn’t ask me any questions. They didn’t hold my attention. They, they, they.

Whose fault is it when a date goes wrong?

When my friends go on dates with my other friends, I hear them say it was “boring”. From both sides. They all accuse each other of being boring. But what it comes down to is not being prepared to lead the conversation. To pivot when they are going down a boring road. To stop before you get to that awkward pause that can completely stop any momentum that may have been building.

First dates aren’t easy or natural for most people, so if you want to get the most out of the date, be ready to make it the best date ever.

Three Tips for Avoiding a Boring First Date

  1. Be Ready With Your Best Ice Breaker Games: While most people roll their eyes while they are in a training that starts with the moderator doing ice breakers, these actually work. They usually center around sharing random facts about yourself, so have those ready. What makes you interesting? What will get you talking about something that won’t be boring?
  2. Glaze Over Your Background Stats: Unless you’ve never talked or messaged with this person at all, they likely know where you work, where you’re from, etc. Don’t spend too much time on these. Instead, share a story about work or about where you grew up. Telling people I’m from a small town in Illinois is boring. Sharing that I graduated junior high in a class of 15 people where the seventh and eighth grade classes were held in the same room sparks a lot of questions. So many questions. So what gets people talking about where you’re from?
  3. Watch for Verbal and Non-Verbal Cues to Change the Subject: It’s really hard to hide being bored. Yawning. Looking at your watch. Checking your phone. If you’re losing ’em, talk about something else. Even if it’s the most interesting thing to you, don’t force it on them. There are plenty of things that will be of interest to both of you, and that is the key. Ask them questions that will help you figure out what to talk about next, like do you think the game will actually be played on Cubs Opening Day? Did you think Green Book should’ve won the Oscar for best picture? Find out what their interests are by asking specific questions that can spark a conversation instead of asking general questions that usually fall flat, like do you like sports? Do you like movies?

If you want your date to be interesting, you need to be interesting too. Sometimes people are nervous or tired or distracted, so they aren’t putting their best feet forward. If you are ready to guide the conversation, you’ll have a better chance of really getting to know them. Of course, you may find that they actually are boring to you. That you have nothing in common. But there will be times when you will see the entire date shift in a great direction. The guy you thought was an egomaniac because he was only talking about himself was actually so nervous that he was just trying to fill the space. It’s worth the effort to bring out the best in people, and they will in turn bring out the best in you.


If you need help throughout your dating journey, drop me an email at or share your question via social media: Hitz & Mrs on Instagram(@HitzAndMrsBlog), Hitz & Mrs on Twitter (@HitzAndMrs) or Facebook. You can also sign up to get my weekly emails or purchase my new dating book to keep you inspired and focused on your goal!

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