Is the past important?

@LENIROSE: Hi, Singlestalk. I’m in my late 30s. I’m anxious to get married. But I’ll never admit that to my friends. I’m wearing a strong-independent-woman-mask all the time. My boyfriend of two months has a checkered past. He’s got three kids from three different women, had a history with gambling all of which happened when he was in his 20s. He’s 35 now and is behaving normally. At least as far as I know, just a couple of partying on some nights. I want to walk down the aisle in a Monique Lhuillier wedding gown soon. Am I just wasting my time with this guy?

DJ: Why don’t you check for Monique Lhuillier’s opinion, too, if this guy makes a good accessory to the gown? Seriously, I don’t want to judge the guy based on someone’s three-paragraphed email. What I can tell you is if your primary goal right now is to get married, you can be more drawn to that dream wedding and it’s tempting to just look away. Stay mindful of the usual red flags.

Is he putting all the blame on the mothers of his children why things didn’t work out? If he is, then he probably has not learned much from a string of trainwreck relationships. Wait, was he even in a relationship with each of them? He’s got three kids. Those weren’t immaculate conceptions. There’s got to be some lessons he learned aside from skills necessary to hop from one bed to another. It starts with accountability. Being a father is a big area of his life now. He must have at least taken the time to pause, think and take a stab at how he can be better this time around.

Does he have a stable job? A person who is always dependent on someone — a parent, relative, friend or partner — has not learned much about running his life. How is he managing his finances, his food, his life? These are issues if he’s already 35. He’s not aging well. You’re a strong, independent woman. Okay, it’s a mask you wear. But it’s not your job to make him a functional member of society. Sure, it feels cheesy when he needs a woman’s touch to bring magic into his world. This isn’t cute, however, in the long run. You’re not his fairy godmother or his ATM card. You’re supposed to be partners in life. Both of you become better because you are together.

Does he take more than he gives? You’re still two months in a relationship but this attitude can already be obvious even when you’re still in that fog of bliss. Does he expect you to carry the relationship? Are you the one setting dates, following through on commitments, initiating couple talks, practically doing most of the work just to keep things going? Why is this a red flag? He likely just wants to feel good and is not that willing and able to work hard with you. Love is patient and kind but not to the point of you having to always play the role of the poor girl down the road. He’s not supposed to bring you down. You’re supposed to be equals.

He probably told you he loves you. Listen to his actions. Not just his words. Now if he doesn’t have these and other stuff which you considered as deal breakers before you met him, give him a thorough consideration. People can learn from their mishaps and when we give them a chance, we allow them to demonstrate this. You want to walk down the aisle in a Monique Lhuillier gown. But a wedding is just a day. Think about what happens next. It’ll define the rest of your life. Reflect and check-in whether this relationship is aligned with your values and the direction you’d like your life to go.

Now if your heart is already telling you that you can change this guy, listen to your mind. That’s my final suggestion. She’s probably now frantically waving the red flags and telling you he probably is not the one for you. Him changing for the better is not yours to make. All the best!