For those of us that enjoy learning about another person, and like sharing stories, playing 20 questions is just plain fun. For others, I realize this exercise is just plain torture. So perhaps to minimize the pain, I can offer these 4 key tips:

1. Know your own story ahead of time.  Try to map out the answers to basic questions about your background, family, work, hobbies/interests, and future goals.  Be aware of what you want to share vs. what you would like to keep private.

2. Have your questions ready.  What answers will best help you determine if this is someone you are interested in seeing again?

3. Own Your Must-Haves— Be aware of the top 5 characteristics you are looking for in a partner.

4. Identify Your Deal Breakers— these are things you cannot negotiate on, which is why we often refer to them as non-negotiables.

Learning my own deal breakers took me a long time, and sometimes I cannot decipher right away whether someone has a trait I’m not willing to tolerate. You cannot always tell within the first few dates if someone has a house in complete disarray, suffers from depression or other emotional issues, is an addict, player, or compulsive liar, or maybe is a financial disaster. There are some things that simply can only be discovered over time.

Usually, people are on their best behavior during the first three months in dating, which is why it is called “the honeymoon phase.” As the glow starts to wear off, I encourage everyone to look at their partners carefully– there might be some traits you thought were dealbreakers, but now you have learned to compromise on certain points. That shows growth and progress, but if there are other traits that you cannot ignore and live with, be true to yourself. Do not delude yourself into thinking you can change another; you can only change yourself. If someone has hit a true deal breaker of yours, you need to be able to walk away– preferably not just by leaving a sticky note or sending a one line text.


By Regina A. DeMeo, Esq.