That Time Aunt Lindsay Dated a Homeless Guy: A Cautionary Tale for My Daughter

Dear Daughter,

I swear I blinked, and you’re already one year old. I watched you looking out the window into our backyard: in your pigtails and pink shoes. I’m afraid that if I blink again, you’ll be driving and dating and I won’t be worried about whether you ate enough vegetables today, but instead about much more serious things.

And because my anxiety leads me to believe it’s never too early to start obsessively worrying about things, I’ve written you this guide on how to tell if the person you’re dating might actually be homeless.

Let me be clear. Homelessness is a serious and complex issue and may be the result of many factors: I don’t mean to downplay that. So instead I’m just going to tell you a cautionary tale based on my own your Aunt Lindsay’s… experience dating a guy I she later found out to be homeless.

You may be surprised to hear, but your ol’ Aunt Lindsay was a firecracker in her day, yes she was. Outgoing, smart, attractive (and gainfully employed), she was certainly a catch for a guy who oft found himself between jobs.

By that I mean he had never actually had one. But did, in fact, own a red collared shirt and some khakis so he could pretend he had one. Oh yes, he was sure to keep his nights free by telling her he worked 3rd shift at Target. Not regularly, mind you. Just every now and then he seemed to have something to do at “Target.”

Aunt Lindsay is a really nice person. She’s a social worker and was born with the heart of one; she gives from a bottomless well of patience and understanding. So when this guy told her he had lost his job due to the unfair discretion of his boss, she believed him. Later, when he told her he should move in with her because he had developed cancer, she believed that, too (he hadn’t). Even when he borrowed her car to drive from Ohio to Virginia to see another girl, she found out on Facebook…and then forgave him.

She stopped hanging out with her friends because they all knew he was taking advantage of her. Then she sort of stopped talking to them for a while. She resented everyone who couldn’t just accept her situation. She began to retreat.

I know what you’re thinking. Aunt Lindsay must be struggling with some codependency issues, right? Well, maybe (aren’t we all?) but that’s not why she continued to date him. He somehow figured out the perfect manipulation: he evoked pity, rage, and sort of fulfilled a need she had to feel like she was helping or fixing or making things better for him (…okay, so she definitely struggled with some codependency issues.)

But what I want you to know, Dear Daughter, is that he got away with all that because it’s easy to lie to a person who wants to believe. Yes, he did some bad things and took advantage of her in a lot of ways. It should be a cut-and-dry bad situation. But it wasn’t for her because in every relationship, there are good times, too: and it was really hard for her to understand how there could be such bad coupled with such good.

So as you get older, and someday start dating, and you start to feel like something in your relationship isn’t right, first of all: tell me. Because I promise you that I (or one of the many women in your village) have been there. And secondly, don’t wait for the bad to outweigh the good. Know your worth, baby. Relationships are hard, but you don’t have to suffer, and you are worth so much more than being somebody’s ATM. You’ll figure out your own definition of what you want love to be, but at the very least, your relationship should not be something you are ashamed of.

FAEVFTT6YMI had a professor once who told us to make a list of what we want in a partner because once you’re in a relationship, you’re in and your judgment is clouded (people and relationships are super complex). I did made that list back in 2003, and it took me about another 10 years to figure out how to stick to it. But I finally did, and when you’re dad came along, it was game on. We help each other and there’s nothing better than feeling like your partner is your power-team.

So that’s our tale about Aunt Lindsay and her Homeless Boyfriend. Now listen to what I’m about to say because it’s really important: if your cousins ever try tell you this story is about me, and not her, you need to know something…

They are liars. They lie all the time. It’s a problem and they’re working on it.

Love you!


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