Questions To Ask A Guy (from a guy)

Women don't ask the right questions. I know some of you are thinking "All I do is ask questions." Well, if they're not the right questions then it doesn't really even matter that much now, does it? You can't just ask random questions. And, if you're not really listening then that doesn't matter much either. You see, most guys have figured out by now that when we open our mouths, that's when things usually go south. The other thing we've figured out is that women tend to love a guy who listens.

Hmmm, best of both worlds? Keep my mouth shut and don't let anything stupid slip out and act like I'm listening - she'll fall for me instantly.

Based on these very simple, basic, behavioral assumptions we can easily conclude how a lot of women might find themselves 6 months to a year down the line with a guy who's suddenly an utter, complete stranger. It's because you either:

a) Didn't ask hardly any questions yet alone the right questions or,

b) Asked way too many questions and didn't listen well enough.

Sure, some things happen that none of us see coming and there's always the exception to the rule. We've all been there before, but this is about the things we can do and hopefully it helps you next time you meet someone new. So here we go...

In my former life, I was something of a matchmaker. There are some very cliche reasons why, which they could probably make movies about, but I'll spare you. Just indulge me. Friends and friends of friends used to bring distressed young women to me like it was my job and from the very beginning there was always an evident pattern. Women would tell me how great the guy was, blah, blah, blah...just before unleashing the big list of red flags...after which I was convinced they had no clue what the right questions to ask a guy even were.

Usually, in first describing him they would be telling me things about his life and not about him or things that transpired, like encounters or conversations and how that made them feel. And, they'd go on...for hours sometimes, if I let them. I never did. Ok, maybe once or twice, but that's because the girl was hot and I was doing to her what the guy before me already did. But, back to the point. I'd finally stop them and say something like "You just told me about what this guy does, how he looks, what he wears, things he says, how he talks and how he makes you feel...but you really didn't tell me one single thing about who this guy is."

Has he ever been in a long term relationship? Is he religious? What kind of family does he come from? Those are the questions you should be asking because you can't know where someone's going until you know where they've been. And, they say history repeats itself, so a little background information can't hurt. I know, it's all rather cliche, but often times we'll look back and wonder how we missed all those red flags.

You see, I think we are all guilty of seeing what we want to see and falling victim to that amazing feeling we get down in the pit of our stomach when we meet somebody we like. Unfortunately, that feeling, which 9 times out of 10 today seems to be the justification of what most women are looking for or why they did what they did in the first place, is unvalidated. It's cute and it makes us feel all warn and fuzzy inside, but it's like hot air - there's nothing backing it up yet. Anybody can seem great when you don't know their flaws or them just yet. And, before you know it, the girl gets caught up in the behavioral tit for tat of dating with the guy and totally forgets all the important questions to ask a guy.

So without further ado, here they are (by the way, these aren't going to be genius or anything. In fact, they're quite ordinary, but if you don't ask them...you won't know them...and later on, down the line, you may realize they could've helped uncover red flags and made all the difference.) Also, it's not so much about the questions as it is about the interpretation and perception that you have based on his answers.

Oh and don't ask these all at once and not all on the first date or first meeting either. Spread it out. Try to work them in naturally - sure he can lie, anybody can lie, but chances are he won't know what the right answer is, so he won't - unless he's pathological, in which case you're on your own. Most likely, you'll probably be able to tell that he's bs'ing and don't text or email these. That gives him time to devise a good answer versus a real, on the spot, genuine one. Ask them in person. (note: Use 'Sooo' because if you do it right then you can be cute about it and smoothly transition into an otherwise serious question, in a non-threatening, non-interview like way)

1. Sooo, what are you looking for?

This one's a no-brainer and should let you know right off the bat where he's coming from, but depending on where you meet a guy (like church or through friends for example), many women might feel a false sense of security and like they don't need to ask this one. Whereas, if you meet him in a bar...then that leads to my #2 question.

2. What do you like to do for fun?

If he says go to bars or hang out with his buddies, then if that works for you good, if not pay attention because this is most likely what he'll be doing 3 months into a relationship. This is also your chance to see if he likes doing some of the same things as you. Often women will complain that men do things like watch too much tv, watch too many sports, work too much, play too many video games, etc, etc. If you're outdoorsey, this is your chance to see if he is too. If you are always on the go, this is your chance to see if he can keep up with you.

Now, if you do meet him in a bar, then substitute #2 for something like:

"Oh, do you come here often/a lot?"

If you do it in a low key, natural way, most guys won't even realize it and will answer it honestly. I once saw a girl smitten by a guy who she'd just met in a bar and hanging on his every word, while all the while their conversation was being constantly interrupted by different staff people and regulars shaking his hand, giving him a high five or a waitress or bartender kissing him on the cheek. Popular guy, right? Some girls go for that. A few weeks later they were dating and I heard she was stressed because she never saw him on the account that he was always going out...to that very same bar. Gee, I didn't see that one coming at all.

3. Sooo, when was your last relationship?

This one gets sooooo many women in trouble. I think instinctively a guy can't go wrong with this one though, so be careful. If it's been a long time then it'll probably help to know why. Could be that he is a commitment phobe, work-a-holic, player, ego-maniac who puts forth no effort or a ton of other reasons that'll bite you in the you know what. And, yes, yes, yes...there could also be a perfectly good explanation, but this article is about weeding out the bad. Now, if his answer is sort of recent then I'd be trying to figure out who broke up with who and if he's still hung up on her. I see that one so much, it's ridiculous.

Sidenote - I find it so interesting that so many women are like magnets to unavailable men or ones who appear unavailable because ironically, most of the reasons why a man would be unavailable in the first place (again, commitment phobe, work-a-holic, player, ego-maniac, family problems, mental issues, girlfriend, lingering ex, fwb, multiple fwbs, etc.)  are the very crux of what a lot of women usually end up giving as the very reasons for the break-up. In other words, you should probably pay very close attention how how available he is, not says he is. Actions speak louder than words and as cliche as it may be, it's so true, which leads me to Question #4.

4. What's a typical week like for you?

This one's so simple and sounds so generic rolling off the tongue that most women will just hang around to see if they can figure it out on their own. But, because dating is one of those gradual types of things where you don't immediately become a priority to someone, it's tough to get a realistic idea of what a typical week might really be like for him - so just ask. You'll be glad you did. You'll get a better idea if your schedules and lifestyle habits mesh and more importantly if he even has time for you.

Also, depending on how vague he is, you just might be able to pick up on cues that tell if he's trying to keep himself flexible for things other than you - catch my drift? I've read countless studies that say most men cheat simply because of opportunity. How seriously you take this question may very well translate to whether or not you're the type who is too oblivious or passive aggressive about how he spends his time. Not to mention, giving what might turn out to be a scum bag a free pass without even knowing it.

Now, even if his intentions are genuine, pure and true, the timing just may not be right or the chemistry that you thought was there might inevitably be overridden by something seemingly insignificant that you skipped over in the beginning. So, out of the 5 questions, that's why this one is probably the most underestimated one on this list. You always hear stuff like "In the end, it was the small/little things." A lot of us have these laundry lists, deal-breakers and "big" things we're looking for, but the irony is, the little things are there 7 days a week. You can't escape them. Who cares that you guys (in a high pitched, lovey dovey voice) "do the same exact things on Christmas" if you wanna strangle him Monday through Friday?

5.  Finally, The Secret Sauce Question

I'm going to give away the bank with this one. Some guys (probably the players) are probably gonna be ticked that I even brought this one up. Other guys (most guys), they probably do this instinctively and they don't even realize it. There's no set question for this one. You might have to come up with one or more of your own, but for your own good, if you value your time - you better figure it out. I've had women tell me that it's too much thinking and shrug it off like they shouldn't have to do this. Um, ok. It's your life, your heart, your dog (unless you bought it with him), your place (unless you moved in together), your sanity and your bed you made if you don't.

Basically, you have to try to figure out where you are in the rotation. Yes, I said rotation. Different guys have different meanings for this word, so I'm using it in the context that most guys (unless they're hermits) are already talking to, dating, sleeping with, pining over or being chased by someone and if you don't at least acknowledge that, then don't be surprised if things suddenly change or don't turn out how you expected.

I once explained to a successful, beautiful, brilliant young lady who was totally convinced that she was this guy's ideal woman...how that wasn't necessarily a good thing. Turns out the guy ended up getting into a relationship with a girl he was already sort of talking to - after my friend's friend had already gotten invested. She was so confused why he would do that if in fact she were his ideal girl or dream girl and I told her that regardless of what his reasons were, I could tell from his actions (via her telling them to me) that he must've been talking to someone else. She ignored those very same signs though and acted as if no other girl(s) existed, when clearly they did.

So anyway, the moral of the story is this: It's very exciting when you meet someone new who you really like and are interested in, but try to keep your head out of the clouds and ask the right questions...and when he answers, really listen. It might save you some time and heartache, in which you could be meeting the guy who you don't have to ask those questions...because he'll gladly volunteer the pertinent information or you'll see it clearly in his actions.