Previously homeless. Red flag?

Author: Single. Approachable. Girl.
June 27, 2010

I do not consider myself judgmental. I like pretty much everyone – with exception to people that purposely try to hurt me (fairly rare) or people with really limp handshakes (drives me nuts. I mean, seriously. Firm grip or bust.)

So it didn’t really occur to me to second-guess one of my current daters when he told me that he lived out of his car for 3 months a while back.

My initial instinct was to think “that’s strange and sounds horrific, but now he has a great job and lives in a 1-bedroom apartment…”

My girlfriend begs to differ.

“So he told you he was previously homeless on a first date?”

S.A.G.: “Well, it’s not like he slept on a bus-bench with a shopping cart, but he didn’t have an actual home, so I suppose you could put it that way.”

My girlfriend: “Was it some sort of social experiment? Did he do it on purpose to prove a point?”

S.A.G.: He didn’t put it that way. He just said matter-of-fact, ‘I lived in my car for 3 months when I first moved out here.’”

My girlfriend: “And that didn’t strike you as a tad odd that he didn’t have any friends with couches or family that would lend him money?”

S.A.G. “You make a decent point…”

My girlfriend: “Not sexy, my friend.”

My friend has me taking a second look at this dater, but I’m still not sure this is a deal-breaker. At least he isn’t trying to hide anything. Similar to the guy from “Let us pray,” he’s laying it out on the table during date #1 and letting me do what I will with the information.

Shouldn’t he be considered a success story? He started in Los Angeles with nothing but an old beat-up SUV (which he still drives despite his great job) and is now living the American Dream. I could see him on the Today Show with Matt Lauer explaining how he worked his way up from the streets of Santa Monica to what some would consider a dream job.

I mean Danny Bonaduce was homeless at one point.

Ok. Maybe not be the best example. But, according to, the following, now-successful people where once homeless: Jim Carrey, Kelly Clarkson, JeanPaul DeJoria, Hilary Swank, Shania Twain, Martin Sheen, Jewel, Kelsey Grammer, John Woo, William Shatner, Heather Mills, Daniel Craig, Lil’ Kim and Drew Carey.

So what do you think? Is previously-homeless guy endearing? Or should he be categorized under previously-dated?


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4 Responses to “Previously homeless. Red flag?”

  1. Ashley Says:

    Dear S.A.G,

    First, your blog rocks ! And I feel like you’re my girl-friend that I know since a long time, just ‘coz you’re sharing your dating experiences, and we women have similar discussions with our girl friends.

    So, girl, if you asked me ( which you did :-P ) please learn a little more about the guy, before crossing him off. I don’t necessarily see that as a red flag.

    On your next meet, tell him you feel it’s awesome that he made it from being homeless at one point to what he is now. Tell him you only read about people who made from homeless to successful like the list above ( btw, you’re awesome in getting the list ), but you never met one, and you’re curious to know more.

    Ask him if he couldn’t get any financial help.Ask how he survived the tough times. I don’t think he’d be offended to share more, ‘coz obviously he shared the topic, and that tells he won’t be apprehensive to share more if you asked, based on the tone with which you ask. Just sound curious and not judgemental. It’ll be perfectly fine. Also it’ll be a great way to know a lot more about the guy’s personality, thought process which is really what dating is all about.

    Also, your girl friend seems to have got scared at the fact that he was homeless, and she seemed to jump quickly into conclusions.

    I’ll tell you about me.

    When recession hit me and I went jobless for few months, I could have borrowed money from family or friends, but I survived on beans, rice, potatoes and eggs for few months. I did so, ‘coz I don’t like to get financial help from anyone. ANYONE. This could be bad or good, but that’s me.

    Now I can buy anything I want, before and after this tough phase, I’ve always been pretty successful career wise, just the recession had me for few months. So it was just a short phase in my life where I had to compromise on food ‘coz I’ve to spend my savings for the apartment rent, ‘coz I can’t ask anyone to let me stay in their home, even if there were lot of options and even when some of my friends offered to do so ! If it was my best friend, I’d have stayed with her, but they were just good friends, not really very close emotionally.

    So yeah, I’d know a lot more about this guy, if I really liked him ( sans this homeless thing ), before I cross him off.

    Good Luck and Keep us posted on how it goes.


  2. Ashley Says:

    Btw, this guy sounds cool to me.

    1) He knows how to overcome tough situations and succeed in life.

    2) He’s honest to let you know his bad times, instead of bragging to impress you about his current state.

    3) I’m not sure about this one, but he seems sentimental about stuff ( he still keeps his old S.U.V.), which tells me he’s capable of emotional connection with things, and may be? It’d apply to people as well.

    Hey, btw you could pass on a casual statement like – you must be really like your S.U.V a lot. He’ll tell you why he’s keeping it. Just get as much info about this guy as you can, ‘coz to me he sounds very interesting.

    In case you choose not to go out with him, please do give him my email. ;-) J/K. Wishing you great things in life.


  3. A guy in green Says:

    Its a shame what kind of stigma being homeless for a little while can leave on a person. I can assume it comes from the fact most are seen as dirty vagrant wanderers who sleep in the streets and try to wash your car windows with bottles of god knows what for your spare change. Ok so maybe some of them are, however plenty of them are just average people who caught a real streak of bad luck and just try to hang on till things turn around. Kudos to the guy for managing to pull through it in todays economy. If just being homeless for that short time is his only fault then I wouldnt give it a second thought. Then again maybe he if he didnt give a reason why maybe he just couldnt find a place he could afford at the time. In example, Im in the military. Some of the people Ive known have done the same thing during unit build ups because they just cant find a good place, housing is overbooked, and all their money has to go back home to the wife and kids. Not quite the same thing I know but hey its an example. This is definately one of those things you cant really judge without knowing the whole story. If he is a good guy, and is squared away I would say he deserves a chance. Just a random strangers two cents.

  4. Single. Approachable. Girl. Says:

    Thank you for all of your thoughtful comments and insights on this topic. While I thought this would make an interesting blog discussion, I will tell you that I did not plan on tossing this guy aside. It takes more than that to scare away this chica.

    That said, I did recently learn he was merely inbetween housing and not sure where to settle down in LA, so he couch surfed with friends and kept most of his belongings in his car. So when he said “lived out of my car” he didn’t mean it in the literal sense. Woops:) Turns out my initial instinct to disregard his statement was right on.

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