Questions I wish I’d known to ask

I wish it weren’t so, but I’ve found that there are some questions I would have never thought to ask, that in retrospect, I would have been better off asking.

I’m not sure I’d have the guts to really ask them, as who would have ever thought it would be necessary? But I’ve found that even midlife men with good jobs sometimes have forgotten (or never learned?) some basics.

Here’s what I wish I had asked:

  • Are you married or living with someone?
    While I have no proof that anyone I’ve gone out with was either, I became suspicious of one who wouldn’t allow me to visit his home, even after seeing each other for 6 months. There were no other indicators that he had another woman, but it would probably be best to ask. Some women make this a standard practice on the first date when they’d like there to be a second.
  • Do you live with one or both parents? Grandparent(s)?
    I’ve gone out with two men over 40 who I later learned lived at home. It would be one thing if they took in their parent who needed assistance. But both these men were still living in their able-bodied parent’s home.
  • Do you generally think people are good?
    I went out with a guy who I discovered made racist, ageist, weightist comments constantly. He continually called people idiots and morons and got testy with waiters and retail staff. This was so off-putting, I quickly ended our seeing each other.
  • Do you have a car?
    While in some metropolitan areas it is folly to have a car, where I live it is nearly a requirement. I don’t envision myself taking the bus on a date or always taking my car. I’m not fussy about what kind of car he drives, but unless he has a medical condition that prevents him from driving, a car shows responsibility.
  • Are you taking medication for emotional issues? Physical issues?
    I am surprised that this has come up more often than I would have thought, especially the medications for emotional issues. I want to know what is going on with someone so I can better understand their behaviors. It’s fine that someone is taking medication for whatever reason, I just want to have the full picture.

Now we come to personal grooming and cleanliness habits. Again, you couldn’t really ask these, but it is sad when you discover their habits so radically different than yours.

  • Do you clean out and wash your car at least once a month?
    Spent fast food containers littering the car are smelly and ugly. And washing the outside every so often shows pride in ownership.
  • Do you clean your house more than once a year?
    I went out with a lovely man for a while and was taken aback when I visited his home. The cobwebs in every corner were as thick as ropes. Going barefoot was uncomfortable because of all the debris on the floor.
  • Do you bathe more than once every 3 days?
    Yep, I went out with a highly educated man who I discovered only showered once every three days. Yuck!
  • Do you brush your teeth more than once a day?
    I brush after every meal, which I realize is a bit fastidious and most people don’t. But when working, I interact closely with people and want to have fresh breath. A guy who only brushes once a day doesn’t.
  • Do you wear clean underwear every day?
    The non-daily showerer also didn’t believe one needed to put on fresh undies each day.
  • Do you wear ironed clothes?
    The rumpled look has no appeal.
  • Do you buy your clothes anywhere other than Goodwill and thrift stores?
    Occasional thrift store treasures can be fun. But if that is the only place you buy your clothes when you can afford more, there is a problem.

If you are able to figure out how to ask these last questions without it sounding insulting, let me know!

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6 responses to “Questions I wish I’d known to ask”

  1. Rachel Sarah Avatar

    Great Questions Dating Goddess!

    Re: the cleaning factor, here’s my deal:

    I recently agreed to move in with my boyfriend — who’s very far from tidy! — after he vowed to hire [and pay for] a cleaning person every other week.

    My six-year-old also got a “responsibility chart” to keep her on top of her own mess.

    So far, the cleaning crew is working like a dream. I’m still having to get on the kid, though.


  2. uewoso Avatar

    All these questions are good and I would add one more: May I see your driver’s license? You really might not know who this person is. If a man is any good, he’ll understand and show it to you with a laugh. If he gets angry or declines… click NEXT.

  3. Elena Avatar

    With regards to the “married or living with someone question” I’ve learned to be extremely specific and direct because of a married guy who was misleading in his initial email response to my ad. He said that he moved to New York City from Boston after his marriage “broke up.” I assumed that meant he was divorced. Nope. I didn’t find out the truth until the second date when I casually asked how long he had been divorced and that’s when he told me he was still married. Turns out that he and his wife had separated four years earlier and were living in two different cities but they were still legally married and owned property together. When I asked him why not divorce, his response was “It’s complicated.” When I pressed for more info, he finally admitted that there were still feelings there and that he and his wife were at an emotional impasse. They weren’t happy together but neither one wanted to pull the plug on the relationship. In either case, I wasn’t interested in becoming a future casualty, so I hightailed it out of there before getting sucked further in.

  4. Rita Avatar

    These questions remind me of “rule” a friend mandated for his teenaged daughter. After her boyfriend rolled his car, the rule was that she had to look at the tread on all four tires before getting in a car with anyone. Not only was this a matter of safety, my friend felt that someone who didn’t keep his car maintained would let down in all other areas of life, since, according to him, cars are the most important part of men’s lives.

  5. Mitsy Avatar

    I dated a guy for 3 1/2 months who was separated from wife #2 earlier this year. He was upfront about where he was in the divorce proceedings, but that got put on the backburner when ex-wife #1 decides she wants custody of the 13 yr. old daughter. He never gave me any reason to believe he would not eventually divorce wife #2 who treated him and his daughter badly. Sadly, he made some really foolish decisions with the stress of the custody battle. He went BACK to estranged wife #2 and did not even have the guts to tell me he was doing this. His sister phoned me about a week later to tell me. She was also furious as she had helped with the raising of this daughter and their whole family could not stand wife #2. They all believed I was the best thing that ever happened to him. I probably was, but I learned some valuable lessons from this little affair. First and foremost, make SURE they are divorced before getting involved with them. My better judgement told me to not date a married man, but he lived locally, I was lonely, and I was not meeting other eligible men who were within driving distance. I cared about this guy a LOT and he broke my heart completely.

    Secondly, it told me just how distorted his thought process was to go back to a woman he supposedly despised and who also made it clear that she was not a fan of his daugther’s. I pity that poor daughter. She was shuffled between 3 homes during the time I knew her. I have no idea where the custody issue is. I have remained friends with this man’s sister, but she has had no contact with him either. If I were a judge, I would not let her stay with her immature Dad and hateful step mom. Very sad deal.
    I KNOW that I dodged a bullet, but it has taken me a very long time to totally convince myself of that. Things did not have to turn out like this, but I will never again date a guy who is not divorced and been divorced for at least 6 months.

  6. Marina Avatar

    While I wish my ex-husband’s mistress had asked if he was married, the reality is she knew we were still married, and she dated him anyhow. My ex claims that he didn’t start seeing her until after he moved out. But as I look back, the evidence says otherwise.

    Even if she didn’t know, I don’t think there is a word in the English language that can describe the incredible shock and pain when you discover you spouse has been cheating on you. It’s like being stabbed in the heart! I spent months wondering what the heck I did that was so wrong that he would just walk out on me. I was heartbroken. I had just lost my sout mate, and I couldn’t figure out why! None of us could. And all the time the divorce was going through the system I begged him to see a marriage counselor because I still loved him and I wanted us back together. Then I find out he did this to me for another woman! She had to have known the incredible pain she was causing me!

    There are a lot of men out there who put themselves out as single when they are not. And even if we ask him if he’s single, a cheating spouse is probably not going to tell the truth. But once you find out the man you’re dating is married the only thing you can do is stop seeing him immediately! Don’t do to another wife what was done to me. And never, ever go into a relationship with a man you know is married! Even if he tells you he’s separated and a divorce is pending. He’s still legally married, and you are standing in the way of a possible reconciliation.

    Nothing good will ever come from going after a married man. Even if you are not aware of it, you are undermining and/or breaking up someone else’s marriage. And it’s true what they say; what comes around goes around. Do you really want a man who cheats on his wife? After all, he cheated on her for you, so it’s not if, but when, he cheats on you for his next mistress.