Real stories about dating and relationships in New York City. Truth is more interesting than fiction.

It Never Hurts To Ask

As I mentioned earlier in the week, I read a LOT of blogs.  Some that you probably wouldn’t imagine I’d be a fan of.

I was laughing my ass off yesterday as I read this post in Very Smart Brothas – How To Answer Questions So That I’ll Never Call You. The gentlemen at are not in the slightest bit politically correct, so you probably shouldn’t click the link if you aren’t familiar with their and offend easily.

I’m just gonna go ahead and quote the beginning of the post, because it’s just that good:

“I’m one of those people that believes when it comes to the opposite sex and dating, you usually get what you deserve.  It’s not to say that if your man cheats on you that you deserved it, but generally speaking, I think that somewhere along the line, you’ve been given some kind of hint as to what kind of person you’re dealing with.

People just don’t ask the right .  We get so caught up in wanting somebody, that we forget that we’d hate it if we ended up dating an axe-murdering serial killer who committed all of his crimes while wearing a pink thong and yelling out “Zorro”.  Thing is, you might know that if you asked about Zorro, haphazardly.  But who does that?”

Smart, right?  And funny.  The rest of the post details some questions he asks women.

Anyway, this got to me thinking about how much I really suck at this question asking thing.  I’ve been trying to get better at it lately.  And I have.  Gotten better.  But I still suck.

I’ve written about this before.  There’s just something about the whole asking direct questions of someone you don’t know well, it makes me uneasy.  Like I’m being nosy.  And I hate nosy.

There is one thing I do make sure to ask, though:

How often do you see/speak to your family? I cannot deal with a guy who doesn’t ever speak to his family.  Conversely, I find myself a little freaked out by the mamma’s boy thing.  But whatever the relationship is, I think it can tell me a lot about a guy.

Other than that -  I’m stumped.  And I don’t think the VSB questions would do me much good at all.


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14 to “It Never Hurts To Ask”


  1. SpikeTheLobster says:

    I’m the other way around, in a sense. I couldn’t bear being with someone who sees their family regularly – I have little to do with mine. I’d always be there in an emergency, but that’s it. No interest. They have their lives, and that’s fine.

    I think the only question I should have asked all the girls I’ve dated (all four of them) was “Have you ever been in therapy, should have been in therapy or been committed to a psychiatric hospital?”

    Unfortunately, they’d all have said “yes” on one or more count.

  2. MakesNooSense says:

    Did you read Steve Harvey’s “Act Like A Lady…” I thought it was a pretty good. A little too much religion in there and sorry but NO ONE waits 60 days for sex but after that there was a part about asking questions. Like you, I don’t want to be nosy or have it feel like an interview. If you did not read they are Q1 What are your short term goals, Q2 What are your long term goals, Q3 What are your views on relationships, Q4 What do you think about me? Q5 How do you FEEL about me?

  3. starangel82 says:

    I’ve always liked asking, ‘tell me a little bit about yourself’ even if we’ve been talking over email for a while. If they balk, I just ask them to indulge me. Hearing how a person answers that questions can tell you a lot about them. One guy launched into a tirade about work and I assumed (correctly) he was a work-a-holic. I’m not saying it’s fool proof, but it is a good icebreaker & get-to-know you question.

  4. MimiCruz says:

    You’re totally right about the family thing- and about asking direct questions.

    I’m dealing with this thing right now- the N.L.D.C. wants me to be “more direct”.

    Sometimes, it’s just hard.
    Friggin ay.

    I did just post something about “The Five Questions Every Single Girl Should Ask”… misunderstood the scenario, apparently the questions are for “him”.

    Check it out… LOL…might help, I don’t know. ; )

    I do always seem to ask, when in bed, (maybe I should ask before I even get close to the bed) if the person’s been with a guy or at the very least “interested” in a guy.

    I never understood the gals who get with guys, who then break up with them for a “guy”.
    Like, how did you not know he was gay from the start??!!!

    Anyways- thanks for the lovely post.

    Mimi
    xx

  5. SINgleGIRL says:

    -Spike
    I guess you can say I’m weird about the family thing. I love New York and am a native and so my family is all very close (physically). But unless something big is going on (holiday, death, wedding) I don’t see them often. But I can’t deal with people who say, “I haven’t spoken with my father in 10 years.” That, to me, usually means someone who is unforgiving and isn’t able to work through problems. At least, usually. I guess I could imagine a good reason or two for completely cutting one’s family out of your life. As to the therapy thing, I don’t know if I could ask that.
    -MakesNooSense
    I haven’t read the Harvey book. Just a lot about it. Yeah, those are questions I couldn’t see myself asking. And I think I’d flip out if someone asked me them.
    -starangel82
    Now that is something I DO ask and all of the time. I’m fine with the fuzzy open questions. And yes, men do reveal quite a bit about themselves when you ask this. But I wonder if specific questions could be useful (I do love the VSB take on it ).
    -MimiCruz
    Haha, I read your post last night just after I finished writing this. I loved it. And speaking of not knowing a guy is gay from the start – I have a post in the post bank (I have a bunch of pre written posts waiting to go, in various stages of done-ness) on that topic. I have sadly been there. I wholeheartedly concur – the bed is not the place for question asking.

  6. Veka says:

    Thanks for the link, I got a good chuckle out of his responses!

  7. wwfchic says:

    See I hate when I get asked the family question. I haven’t spoken to my Dad in 10+ years (with good reason – seriously) and my Mom left when I was 7 so she’s not the “Leave it to Beaver” Mom by any means. So then I try and explain that we aren’t that close and I get 20 questions and then I think – do you REALLY want to know?????

    So I avoid that question.

    I also write a food blog – so my big question to ask is “What is your favorite restaurant?” If they say a chain – THEY’RE OUT!

  8. Anonymous says:

    Oh yeah. Having done my share of field research, here is one. Check how their relationship is with the parent of the opposite gender.

  9. Shannia says:

    i like to know what the ex did for a living, and sometimes the one prior. I had a guy once tell me his ex was a stripper and the relationship was full of drama but they where toguether 4 years and the one before was a nurse… but then he finishedt telling me this by adding “but she had fake breasts” so clearly this is NOT the guy I want to date, ever!

  10. SINgleGIRL says:

    -Veka
    I’ve been reading them for months and they never disappoint.
    -wwfchic
    Like I said, I know some people have really complicated family situations. And I think I’m sensitive to that. If someone seemed tense about it I would back off. But most of the people I’ve known who don’t speak to their families don’t do it for minor reasons. The restaurant question is a good one. I think I could ask that without squirming. Not too nosy.
    -Anonymous
    VERY interesting. I’m going to have to ponder that a bit.
    -Shannia
    WOW. It would never occur to me to ask that but now that you mention it it might have saved me ALL kinds of drama (of thinking of some of the men in my life and their exes). You are one smart woman.

  11. lostplum says:

    i always ask (or i guess dig) about friends. I’m a social person and need someone who I can take tp an event or out and they can be just as social. Actually had a guy once tell me on a first date he didn’t really have any friends, and the two he somewhat had were “losers”. (this is a guy who has lived in the city for 12 years) Now someone doesnt have to have 100 amazing friends, but he should at least have 1 or 2 that he hangs with. If he ain’t a social ‘friend’ kind of guy, i’m out! It says alot about someone when you know something about their friends.

    I love my parents to death and we get along amazingly but yes talking about parents sometimes puts people on edge, i like to start with siblings. Discussing siblings sometimes can be a nice transition or bridge to the whole family thing, and most times it opens up for it. Also, you can tell alot about a person who is say the oldest, youngest, middle, or say the banker who has 4 doctor siblings.

  12. SINgleGIRL says:

    -lostplum
    Excellent point about the friends. I am not hypersocial but I value my friends immensely and cannot imagine a relationship with someone who was a total loner. Hmmm.

  13. Devon aka Dru says:

    That link was great. VSB is now on my list of must reads :)

  14. browolf says:

    also it never hurts to call people out on stuff they say that either doesnt make sense or there’s obviously more to it. Assuming there’s a good explanation is never a good idea but since truth is often stranger than fiction, cant assume the worst either. give people enough rope and they’ll often hang themselves. aka if they feel comfortable telling you things they tell u stuff they probably shouldnt.
    lol @ looser friends