Let’s be honest here ladies, the older we get in the dating world the more likely we are to encounter people who have a less than stellar track record in a variety of different areas of their lives — money issues, intimacy issues, cheating, divorces, addiction, etc. And while the thought of all or any of the above often sends our “common sense” trigger off in a multitude of ways, there is something to be said for giving someone the benefit of the doubt.
People mess up. Plain and simple. They cheat, they lie, they make terrible decisions, but there are people in this world who can (and do) learn from their mistakes. So, what happens when your new “Mr. Right” was at one time “Mr. Oh-So-Wrong”? How do you know when to take a leap of faith that someone has truly changed and left their scandalous past right there, in the past?
Decide what you can tolerate
Before you even look towards the other person’s wrong-doings, take a good long look at yourself. You have to decide whether or not you are going to be able to deal with whatever baggage it is that this person carries around with them. If your man cheated on his ex, figure out whether you would ever be able to trust someone like that. If he’s made some unwise “financial” decisions in his time, be sure that you will be able to deal with the windfall. And if he’s got an addictive past, make sure you’ll be able to handle the possibility of a relapse. He may be 100 percent sure that his past is in the past, but you need to figure out whether or not you are going to make him pay for those mistakes over and over again for the years to come.
Go in for the kill
If you’ve heard the rumours and you know that there are things about your man who might not be totally “honourable” then don’t be afraid to just come right out and ask. Yes, there is a time and a place to bring up these sensitive subjects (ie. don’t do it on the first date in a restaurant full of people after three glasses of wine) but if your guy is truly trying to change his ways he should have no problem being open and honest about what has gone down and what changes he is trying to make. That said, if your guy goes on the defensive as soon as you bring up his past…be warned.
Don’t be afraid to dig around
Even if your man has come clean about his shady past, don’t be afraid to dig around. Sure it is nice to believe that you will go on an honour system with your new beau, but trust us, if it was you who was exposing some nasty indiscretions, we can almost guarantee that he wouldn’t falter to dip into your past before committing. Now we’re not telling you to go all out and order a police check and financial records — but checking out your man’s social media, his LinkedIn profile, and doing a couple in detail Google searches never hurt anyone. Especially when it comes to making sure his story lines up.