The Best Conversation Starters When Dating After Divorce

As a divorcee, it is so hard to date. Following separation and significant relationships, often our confidence has been shaken and we aren’t sure what is dating protocol nowadays. Many people don’t want to talk about their kids, their divorce situation or work. The topics are either incredibly boring for the recipient or be considered as information overload.

Avoiding topics such as work (which can make you appear superficial) and the weather (which is incredibly limited, not to mention boring) can be challenging but will open you up to learning about your date in slightly more creative ways. The questions below demonstrate whether someone has personal insight, where their sense of self-worth is and what they value in life and relationships.

  1. “Tell me about your best friend.” Who you hang around and who you gravitate towards is often a great indicator of your behaviours. Like attracts like. If you (or the person you are talking to) are able to talk glowingly about your best friend and the activities you like to do together, it shows your date what an interesting person you are and how you are happy to celebrate another person. Similarly, if you hang out with the ‘down and out’ crowd and talk about them accordingly, then it is a strong indicator that you too are headed towards the ‘down and out’.
  2. “What are you passionate about?” Find out what makes your date tick and how they get pumped or motivated. Are they self-driven? Are they living ‘the dream’?
  3. “What charities are you involved in or support?” this shows whether your date is community minded and how involved they like to be
  4. “What did you learn from your previous relationships?” No relationship is perfect, but we can all learn from each relationship. We are all growing and developing. Unsuccessful relationships can teach us about what we do well and where we can improve.
  5. “Describe your relationship with your parents and siblings?” There is an old saying “the way he treats his mother, is the way he will treat you.” Let’s extend upon this: This question illustrates the family dynamics and idiosyncrasies – are they close, open and transparent? Do they communicate well? How often do they catch up? What is quality time to them? It is an opportunity for you to consider how this fits in with your own family forces.
  6. “Describe your parents’ relationship when you were growing up.” Often the way any individual was parented is the way that they default in parenting. We can all work on and implement new strategies. However, when the pressure is on and the stress levels are high, people tend to resort to the way they were parented for the first 20 years of their life (a very impressionable time).
  7. “Are you happy with your work/life balance? Does it need tweaking?” This may demonstrate whether your date is working for a future, working as a distraction and whether they have a high level of life satisfaction with work and non-work activities. It creates an opportunity for your date to open up about hobbies, how they relax/unwind, how they socialise and whether they would be willing to adjust the ‘balance’ to fit in a special person.

As much as there are questions that you can ask so that you can learn more beyond the superficial niceties, there are also taboo topics that should never be discussed in the first couple of dates. These include:

  1. Taboo topic #1: Financials. It is no one else’s business knowing how much you earn, how you earn it and whether you earn any at all.
  2. Taboo topic #2: Politics and religion. Tread carefully here. You don’t want to discuss anything contentious and politics can become a heated discussion very quickly for some people. Similarly, religion can become equally heated and offensive at speed.
  3. Taboo topic #3: Your divorce. Your potential future suitor/partner doesn’t want to know all of the sordid details of your separation and divorce. Save it for a later and more appropriate date. It’s not right sharing your ‘dirty laundry’ with a stranger.
  4. Taboo topic #4: Your deepest, darkest secrets. Family secrets and personal secrets, including hang ups, are not attractive to other people. Sharing these sorts of things should be reserved for only the closest, most trusted people. When your date becomes a part of your inner circle, once trust has been established, then you can share your personal stories.
  5. Taboo topic #5: Your children. (This is open to interpretation and personal perspective) Protecting our children is our first priority as parents. Some people dating prefer not to mention their children in their online profiles or at the first couple of dates (for a variety of reasons), especially if their date doesn’t have children. However, parents dating other parents don’t mind talking about their children because it is an instant common bond. Be warned: don’t talk too much about your kids because there is more to you and your date than just being a parent.

If you are meeting someone for the first time, tell a friend where you are going, who you are meeting and share your date’s mobile number. Check in with your friend after each of your first few dates until you are sufficiently comfortable with them as a person.

Dating is a great opportunity to learn about others and who you are today as well as a great opportunity to get out of the house and your usual routine. Have fun and be safe!


This is general advice only and is not provided as legal advice. If you have a legal issue, you should contact a lawyer and/or accountant before making a decision about what to do or applying to the Court. cannot provide legal advice. If you have an emergency situation, please contact Emergency '000'. © Divorce Pty Ltd