4 Surprising Conversation Starters For An Un-Boring First Date

July 10, 2020

We’ve all been there - the difficult, hesitating and always superficial conversation that carries along first dates. We’re talking, and sometimes listening, but rarely caring. Instead we’re thinking about other things, like if we have food in our teeth, if we’re going to get laid tonight, or if our date is better looking than we are (and knows it). We spoke with Brad Jeffries of Chatline Connect, a phone dating directory and informational site, about how to engage with first dates, either on the phone or in person, in order to get the most out of what could easily be a uninspiring encounter. They responded by giving us a few great conversation starters for having actually interesting conversations.

4 Surprising Conversation Starters For An Un-Boring First Date

  1. “Do you believe in god?” - Okay, so we’ve been taught to never talk about religion or politics if you want to get along with someone. For the most part, that’s sage advice. The thing with relationships, however, is that we want to get beyond ‘getting along’ and into ‘are we compatible’. While you definitely do not need to share your partners religious beliefs in order to be successfully compatible, you do need to at least approve of them enough to respect their position. While we wouldn’t drop this question in the first 5 minutes, we think it’s an interesting way to get into a deeper conversation that seeks to understand what a person is really all about.
  2. “Where do you see this going?” - Yes, this could also be too bold. Then again, it’s good to both be on the same page as far as what you would like to get out of a relationship. The fact is, some people are looking to meet a bunch of people, get their confidence up, and enjoy the single life, while other people are really focused on finding someone they can shack up with exclusively. It’s nice to know if you and your date have the same intentions, so there is no confusion or misunderstanding when/if things start going well.
  3. “What’s your dream vacation?” - People’s daily lives don’t always match up to their truest self. You may be an accountant by day, but that doesn’t mean crunching numbers for corporate client is necessarily an expression of your truest values and desires. The word ‘vacation’ is a way to get people talking about their dreams in a concrete way. It often tells us so much about the person’s hopes, aspirations and sense of accomplishment. For some, a dream vacation is a physical challenge such as hiking a difficult mountain range, while for others it is spending time at home with their kids. You learn a lot about who people really are when they open up about how they would ideally like to spend their time.
  4. “Tell me about your family.” - If family is important to you, you might want to know how your date feels about the role their family plays in their life. Are they in regular contact with mom and dad? If not, why? Family is generally a touchy subject for people, and it gets people talking about some insecurities and difficulties with stories and facts. It works as a way for people to talk about themselves without having to talk about all their personal issues. Additionally, if you are a family-oriented person, you will like to know where family stands in your date’s life.


While we don’t recommend you drop all these in every date, we do hope these get you thinking about ways to engage in a deeper and more interesting way with the hopefully fascinating singles you meet out in the world.

linkedin facebook pinterest youtube rss twitter instagram facebook-blank rss-blank linkedin-blank pinterest youtube twitter instagram