Dating with a checkered past

Checkered Past

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It is easy to pass judgment on someone's past, but in dating, it is not where you are coming from—it is where you are going. An unknown past can be scary when you first start dating and you may ask yourself, is this person genuinely good, or do they have skeletons in their closet? Although a legitimate concern and one that does deserve study, it is unfair to judge someone's worth exclusively by their past, and it’s unfair to yourself, too, if you are discounting a potential love match before giving it an open-minded and honest chance.

Could you overlook a person's past if you found out they had at one time participated in a polyamorous relationship or engaged in homosexuality? What if a mother surrendered custody of her children or a man committed a theft, or had spent time in jail? These scenarios would all cause serious concern for a relationship candidate, but again, it is not where you are coming from, it is where you are going. The amount of self-reflection, growth, and internal work a person has done should carry more weight than a checkered past and hold greater influence on your dating decisions.

During my matchmaking with Perfect Search, I had a client named Tony who was concerned about Natasha, a woman I introduced him to. Natasha had surrendered custody of her nine-year-old son to her ex-husband and moved to the USA from Russia. After learning those facts, Tony wasn't sure if he should continue dating her. I encouraged him not to pass judgment on her since she had shared with me the details of her previous suffocating and controlling marriage. Although her ex-husband was an intolerable husband, he was, however, a good parent and good provider for their son. Rather than uprooting her son from his stable home and school environment, Natasha determined that her need to grow and explore as a woman could be done by leaving them both and moving to America. Although it may not have been the choice for many mothers, it was a rational choice for Natasha and should not have immediately indicated a flawed personality.

Another example was a story I heard from a man who was driven and ambitious, but born into a troubled family. He had grown up in a rough neighborhood and had spent time in jail for several petty theft charges. He was tenacious, scrappy, and conniving as a young man and lacked morals in many of his early decisions; but through self-refection, therapy and honest analysis, he was able to overcome the opportunistic methods of his past and achieve success by channeling that creative energy into the positive business practices that now reflected his current success. If someone were to ask him about his past, he was always honest, which scared many women he dated away. After all, who wants to date someone who has a rap sheet? But again, my opinion is that it is not where you are coming from, but where you are going.

Another woman who joined my candidate pool was dumped by her boyfriend when she confided that during her 20s, she had been in a polyamorous relationship with a man and another woman.  The three of them lived together, loved together and slept together. It was an experimental phase in her life that was satiated with time and was no longer relevant. However, her current boyfriend could not cope with the history and abruptly ended their relationship when she told him.

So, how much information about your past should you share, and when should you share it with a new love? Should history be a mystery, or is an open book the best policy in a relationship? The answer lies somewhere in between. It is best to be preemptive and share a checkered past with your love, or you run the risk of them finding out and being shocked (as in the polyamorous example) especially if it is something that you will want to discuss as part of intimacy and sharing. However, telling someone too soon (as in the jailbird story) is not a good idea either. You have to first set the hook and get the other person to fall in love with you before you drop a bomb like being in jail. In situations like that of Natasha, who left her child with his father to live abroad, this should be shared with care and received with an open mind. Remember, it is not where you are coming from, but where you are going.

For more information, contact Melinda Maximova, matchmaker with Perfect Search melinda@theperfectsearch.com