I'm Dating a Single Dad. Help!

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Dear Willie D:

I feel like I missed out on the lesson called dating because I just can’t seem to make a relationship work. I vowed to never date a man with children, yet here I am, 37 years old, after several failed relationships with various childless men. The guy I am talking to now for the past five months has two sons, a nine-year-old in Houston, and a 14-year-old in Miami.

He doesn’t talk to the son in Miami much, and I have never met him, but the son in Houston lives with him. I have seen them interact, and he is a good father to him. But the mother I’m not sure about. I have never met her, but whenever I’ve been around him, and he’s talking on the phone to her, he never gets loud or disrespectful.

But he often becomes visibly agitated by her constant nagging and her trying to control his relationship with his son. I can deal with kids, but I don’t do baby-mama drama. Am I setting myself up for failure by dating a single dad?

Single Dad Recruiter:

I can’t say conclusively that you’re setting yourself up for failure by dating a single dad, but the agitating baby mama don’t help. I’m sure being a single dad can be as tough as being a single mom when it comes to dating, and dating one can come with an array of challenges.

However, be heedful about painting with broad strokes, for it is attention to details that often produces the masterpiece.


Dear Willie D:

I’m a truck driver by trade for the past 24 years. At one point I was able to quit my job and buy my own trucks. Within three years, I had six 18-wheelers. I was pulling in some good money, but I failed to diversify and get into other businesses, so when I took sick, almost overnight, I lost everything.

First, I had two drivers wreck two trucks in one week. Then I had a truck that needed $6,000 in repairs, and business got slow. I had drivers quit on me and employees steal from me. One of the employees was my brother-in-law. My cars got repossessed, and my house got foreclosed on.

After all that, I kept saying, at least my wife is still by my side. Then she left me for one of my drivers. I figure I don’t need people anymore. I’m just going to rely on myself. Why do people let you down when you need them most?

Keep on Trucking:

People let you down when you need them most because they don’t want to incur any emotional contagion or social debt. If they think helping you might cause them to be infected emotionally or that socially you haven’t invested in the relationship enough to deserve their support, they might abandon you.

The funny thing is, I discussed this at length with my 17-year-old son last week. I told him, as much as me and his mom love and support him, we’re not always going to be there for him. One day we’re going to cut him off from our money, and he’s going to have to take care of himself. But more than that, one day we will die.

Because all relationships are temporary, some because of death, some by choice, people are only in your life for a moment. Some moments last longer than others, which is why it’s unwise to obsess over any relationship. Love like you’ve never been hurt, and give loyalty to those who never make you question theirs. But ultimately, the only person you can rely on is yourself.


Dear Willie D:

Why do people disrespect people who give their kids unisex names? Being a female named Logan, my name is often at the center of first discussions when I meet people. I like my name, but most people are stunned to know I’m a female. They assume that I’m named after my dad, a grandfather or “a rich uncle,” which I’m definitely not.

I utterly despise when they try to call me Lo for short because it sounds better to them. The double standard is so stupid to me. Your son can be named Blair, but my daughter can’t be named Carson because it’s too masculine? That’s a bunch of crap. I don’t get it.

Trading Names:

Generally speaking, the people I know personally who have unisex names wear them well. But to name a girl Bruce or a boy Debbie would be cruel and unusual punishment.


Dear Willie D:

The country of Haiti is in ruins, and in need of international intervention. Since the U.S. considers Haiti a policy priority, and it’s so close to our borders, if I could show you irrefutable evidence to support why both nations would be better off with a merger, is that something you would support and get your followers behind?

Better Off:

Absolutely not. If the U.S. is truly interested in helping Haiti prosper as a nation, the best thing to do would be to aid Haiti in being firmly rooted in democracy designed to build a strong nation that fosters sustainable growth, sound infrastructure and economic development for the people of Haiti.

Haiti doesn’t need a handout, it needs a hand up.

Ask Willie D anything at willied.com/ask-willie-d, and come back next Thursday for more of his best answers.

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