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10 Questions To Ask Your Boyfriend (If You Want Him To Run)

Women are constantly testing us.

It’s a fact.

They do it not because they consciously want to – they do it because nature forces them to do so. It’s hardwired in their brains since Early Man. Nature has made sure that the only children to survive are the healthy and strong, to ensure the overall survival of the tribe.

So women have to be extremely picky. Even today. Especially today.

By the way, we men are "brain wired" too when it comes to selection for mating. Why do you think that we prefer large breasts?

Most women have cultivated a deceitful detection system that can spot freaks and wackos. Some have taken this to a level of perfection. They smell if the wrong man is around them.

What is their secret weapon, their scanner for unworthy sperm donors, you might ask?

They use questions (among other things).

The best of them are asking questions, all of which you NEVER would have guessed as to what’s really behind them. They are masters of love-profiling. If you make it through their test, you really are the "King of the Cave".

But sometimes you will encounter women who are, let’s say it carefully, not so skillful when it comes to choosing the right questions to ask. Their questions, although having an honorable intent, unfortunately have the effect to scare the men away, or even to make them run as fast as they can.

Not quite the outcome nature has hoped for.

I’ve compiled a list of all the best of the worst questions to ask your boyfriend for your amusement and determent. Ask them, and you will see him run (if not, then you’d better run!).

So, here they are:

The Top 10 List of the Questions to ask your Boyfriend (if you want him to run)

10. Do you like my bottom?

This is a classic. Who has not heard this question in his relationship at least once?

A very attractive woman once said to me: "If we ask you how big our bottom is, you’d better tell the truth. If we ask how big another women’s bottom is, you’d better lie".

You could get in trouble with a wrong answer.

9. Would you like to go shopping with me?

Uhh, this hurts. Going shopping with a woman is always pain.

The trick is to find the perfect middle between, "this dress looks perfect on you", and "buy this if you want to go hooking".

8. Do you mind if your best friend joins us in bed?

No comment here.

7. If we were a Hollywood movie-couple, who would we be?

This is a question only a woman can think out.

The answer on this one? You better find a good one. I’d say "Beauty and the Beast". Leave open who the beast is.

6. Have you ever cheated on a girlfriend before?

Trick question.

This answer to this one is of course "Me? I would rather die!"

5. What would you do if you were alone in the Playboy-Mansion with 250 Playmates and all are famished?

Yeah, of course: "one must feed the hungry".

4. How many people have you had sex with before me?

Don’t mention that you’ve been in the Playboy-Mansion before.

We all know what happened to Don Juan DeMarco when he confessed to Donna Anna.

Don’t do it!

3. Can you explain to me how to handle a [complicated technical device]?

Have the patience to explain or send her to an electronic store. Choose wisely.

2. Will we be together forever and marry one day?

I was asked this once after 2 months in a relationship. Man, I didn’t know that I could run so fast.

And the Number 1 of the questions to ask your boyfriend is:

1. Would you tattoo my name on your upper arm?

That’s it. The worst questions to ask your boyfriend.

If you as a girl have asked one of these questions before, I would suggest that you train your skill a bit more. These are absolute no-nos. There are plenty of questions you can ask without scaring your boyfriend away.

As for you guys, in another article I will teach you how to handle and react best to these annoying testing-questions.

Until then, weigh up every answer. A wrong one could get you into deep… trouble.

Your friend,

Eddie 😉

P.S.: If you want to learn some “real” questions to ask your boyfriend then click here.

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51 Responses to 10 Questions To Ask Your Boyfriend (If You Want Him To Run)

  1. Maria Agabalyan February 12, 2008 at 3:31 am #

    Thank you for the break up advice.

  2. Hot Alpha Female February 29, 2008 at 9:22 am #

    Hey Eddie,
    I just came across your website and I think its fantastic! There is so much good content on here, im clicking on so many things like a mad woman! LoL

    Neways in regards to these 10 questions that a chick shouldn’t ask. I think that you are pretty spot on.

    Some questions that I would add to the list swell would be

    Where do you think this is going?

    Do you love me?

    Don’t you want to get married, have 2.5 kids and settle down with me?

    Who do you think is better looking .. me or (some other random chick?)

    I think the point that im trying to make here, is that the one thing that turns any guy off is a needy and clingy chick.

    From what I can tell, guys really like to be in relationships with girls where they don’t feel like they are being pressured to act a certain way, to commit to certain things and do things that they don’t want to do.

    They like to believe that they have control over their own life and how the relationship is progressing.

    The worse thing a chick can do, is come across as controlling and insecure.

    But its ok, because there are way to tackle these insecurities. Its sometimes natural to want to get your man and hold onto him for dear life.

    But its also at these times, where we really need to focus on our selves and remember to do something that makes US happy and that makes US fulfilled.

    Girls these days need to stop thinking that some guy will make them happy and make them fulfilled. That’s not your partners responsibility.

    That’s your own ….

    Hot Alpha Female

  3. Eddie Corbano March 3, 2008 at 7:36 am #

    Hey HAC, thanks for the kind words and for commenting.

    Yes, these questions are founded in insecurities, it’s important to realize that.

    Guys should really address them playfully with joking, never give a direct answer.

    Eddie 🙂

  4. Elena May 28, 2008 at 9:10 pm #

    Ok, so great to know that i just screwed it up with a couple of those “run away” questions – listed by HAF. I did ask “Where do you think it’s going” and “Do you believe in our future” – and that’s when my boyfriend got really distant and thoughtful, and finally said he wants more space and he is tired… But guys and gals, listen, shouldn’t a couple have an honest talk about their future, after being in a relationship for 4 years? If you don’t ask these questions, how can you make sure YOUR needs are respected? Yes, you can communicate with your boyfriend “indirectly”, but you can’t do that ALL the time!

    • jemima January 18, 2016 at 5:39 am #

      damn i understand where u come from clearly he didnt want to have a future with u

  5. seven August 20, 2008 at 6:07 pm #

    wow these are awesome questions some were very disturbing in my opinion but for the most part i loved them
    now i have many questions to ask my bf when he makes me ask questions cuz his lazy butt is to lazy to talk…haha

  6. Mimi August 25, 2008 at 6:07 am #

    lol nice questions, but I asked the #1 question to my bf and he didnt mind, he said yea.
    he evens brings up marriage and kids sometimes, :S odd boy he is, but i love him hahaha =D

  7. lalala September 16, 2008 at 5:30 pm #

    Have you ever done something embarassing in front of your girlfriend?
    Is cheating on your girlfriend ever OK??
    Would you be unfaithful if you knew your girl would never find out?
    Would you let your girlfriend take naked pictures of you ? How about a sex video?

    Have you ever rented an X-rated movie?
    Do you own any porn magazines? Can I see them?

    Have you ever sent a naughty text message that backfired on you?
    Have you ever gotten it on in a car?
    Have you ever scratched down there when you thought no one was looking?
    Have you ever regretted a hookup ?
    Have you ever had phone sex?
    Do you believe there is one soul mate out there for you?
    How long did it take you to get over your last ex-girlfriend?
    How many sexual partners have you had?
    How important is religion/ethics to you?
    Do you have any STDs?
    Do you use drugs?
    How much TV do you watch?
    Have you every shoplifted?
    Do you drink while driving?
    Have you ever driven a car while drunk ?
    Have you ever committed a crime?

    • Eddie Corbano October 7, 2008 at 10:08 am #


      Good questions, my favorite is: “Do you own any porn magazines? Can I see them?” 😉

    • Ortiz Zuzy September 14, 2010 at 3:07 am #

      i personally think this will have your boyfriend running before you finish the question.

      Can get married first and then have sex?

  8. Satisfaction January 10, 2009 at 4:42 pm #

    Very nice article. These questions were interesting to read and to see how you had responded to them. It does seem true that like 90% of all guys have this way of thinking, and I agree they would probably get a bit uncomfortable or confused when being asked these types of questions by their significant other.

    I’d however like to boast (in the most humble way I possibly can) about how my boyfriend is one of the few 10% whose personalities are completely contrary to the theme of this article. I read these questions to him, and he laughed it off good. All of these questions he could answer without hesitation and with openness, with honesty, and surprisingly, all of his responses were to my favor, not because he knew I wanted to hear it, but because it was truly what he thought.

    People say guys don’t like to feel like they’re being interrogated with strange questions like these.

    I’m happy that my guy is someone who is open about anything he talks about. In fact, he was the one who told me today to look up “questions to ask your boyfriend,” just for fun while we were talking on the phone, so that I could learn more about what he’s like.

    I know the point to this article was to help readers see something completely different as to what I’m saying, but I still thank you so much for helping me further realize how lucky I am for encountering a man like the one I have today.

    My apologies if this comment has total irrelevance and does not belong here, and also if it may have offended anyone by some chance. I just want to express to the public how lucky I am and how my boyfriend is the perfect one for me. It took me a long time to find him and I want to be able to say this for once. Every girl can find who they are looking for if they are patient and take effort into it.

    • Eddie Corbano January 12, 2009 at 12:33 pm #


      Thank you for commenting.

      Originally Posted By Satisfaction
      I know the point to this article was to help readers see something completely different as to what I’m saying

      I tried to accomplish two things with this article:

      1. to make you smile
      2. to help you distinguish good questions from bad ones


  9. three!:] March 12, 2009 at 1:29 am #

    hahahahahahahah! I asked these questions to my bff bout his gf and he got nervous even tho she wasnt there! lol

  10. riette April 6, 2009 at 5:29 am #

    Depesite all these questins…one is still left out….

    Do you think I am better looking than your ex?

  11. Eddie Corbano April 6, 2009 at 8:36 am #

    Good one, Riette 🙂

  12. maurissa May 23, 2009 at 10:10 pm #

    he may be lieing to you don’t fall for that

  13. krincle July 15, 2009 at 11:01 pm #

    hey eddie i just done reading all those questions to never ask ur bf. googd thing i never asked any of these questions. but i had to break up with my boyfriend because i found out he was cheating on me. well it was more like i was the other woman. and we talked about our breakeup. he was more opened about than i thought, but when we talked to his other gf and were trying to talk about it it turned out that she was cheating on him too. i was the one who didnt cheat. it makes me feel more honest then them. do you think that i was more loyal then the way they were treating eachother? thaks for the 10 questions to never ask a guy. : )

  14. dynamiteroll July 17, 2009 at 5:09 pm #

    @Satisfaction – i agree with you completely. in my case, he was the one to bring up marriage and say he’d like to marry me one day. he was the one to say he wanted kids when he was older. in the end, him bringing this up made me feel like i could be open with him about our future, and now we both feel like we’re at the same place, since we know we can talk about where it’s going and how our lives could work out without scaring each other off.

  15. prince February 1, 2010 at 6:46 pm #

    hi eddie im in love with 49year oll married man. We’ve been togethet for 6years now so much memorie and feelings involve. Im in love with him and yet it hurts so much the fact he is married. to think this relationship is going nowhere pls help! im 28yyrs old independent and self sustaining woman. why i end up with this kind of relationship. Thanks

  16. Darsheena February 27, 2010 at 11:10 pm #

    How funny. These things you mention are the exact same things my boyfriend does to me. I’m just lucky I guess. This is kind of stereotypical of both men and women. Men aren’t bastards who pee in their pants because of commitment and women aren’t clingy bugs! We are individuals so there isn’t any tutorial on how to stay in an healthy relationship.. There shouldn’t be any guidebook to love. I believe that these manipulating tricks are the most crucial trigger of so many failed romances..

  17. sara March 4, 2010 at 11:27 pm #

    Just be yourself,
    ovbiously he likes you for who you are now if he asked you out. then there is noo need to change.

  18. i got a man March 6, 2010 at 2:49 pm #

    thx for the 10 questions never to ask a guy but me and my boyfriend asked each other thses questons before l0lz he gave me honest answers too like for question 10.he said he liked mine and he said da otha girls didnt have nothin on me for question 9.he said yes he said he would love to spend some more time with me. for 8.he said no cuz he want me 2 him self for 7.we aint know wat 2 say so we left it blank lolz. for 6. he said no.for 5.he said yes he would feed them lolz. for 4. he say 5. for 3. he told me how to put rims on a car it was borin. 2. he said one day he would defineltly marry me. 1. he getting it on his arm tommorow.

  19. shortie March 29, 2010 at 5:14 pm #

    hahhhahhahahah i wld ask my bf this ?s but i wld be really mad if he was with playboy gurls or if he has sex with any other gurls before me

  20. Selena April 20, 2010 at 7:18 am #

    Thats true but theres other indirect questions you can ask your man even way before you get that far off into the relationship that will tell you whether or not he has commitment phobia so you don’t waste you’re time. I was dating a guy for three years and soon as I mentioned anything about marriage/commitment he went haywire. I broke up with him but he still calls and says he loves me and wants to be together but still he’s not for commitment, I’ve moved on but ask certain discreet questions to potential daters so that I don’t make the same mistake round 2. We only have so much time on this earth and I rather not waste it on a relationship headed on the route to nowhere.

  21. Jennifer April 26, 2010 at 8:40 am #

    Lol… thanks soo much i couldnt help myself i asked my boyfriends all of these.

  22. Koolchick010 June 22, 2010 at 3:55 am #

    my boyfriend and i have been dating for almost 8 months coming up on the 27th. But he upsets me so much saying watever he wants without thinking about my feelings. Like hello i have a soul, too. I think he's getting to “comfortable” with this relationship. But when i confront him about it he claims he loves me. Theres plenty of times he crossed the line. Idk what to do anymore..i try to be positive but when he is “childish” i cant take it..please help

    • Yea yea August 4, 2010 at 9:18 am #

      If you continue letting him doing this to you he won't understand how you feel. He already don't respect you, you gotta put ur foot down and said it enough. talk to him claimly let him know how you feel. if that doesn't work yell at him lol. but seriously guys will never understand you unless you tell him

  23. Avivadiva14 June 27, 2010 at 4:08 am #

    Wow this is a fun little sexist list.

  24. Mz Royston July 19, 2010 at 6:31 am #

    .UqH MAh b0YFRAN iS NoT boyfran material i found out he wuz still going out with his ex after 8 months of our relationship uqh! idk what to do i confronted him about it an he finally told me the truth i wuz really heart because she wuz the gurl he wuz really in love with but i put it behind cause i loved him so much an one day i looked on his facebook an he had he wuz married to her an wen i comfronted him about it and he kept sayn that been there an till this day he havnt changed it i really dnt know wat to do any more the only thing that makes me stay is because he all ways telling me how much he love me and care about me but i really dnt know its more to the story…! HELP PLEASE!

    • Lilly August 4, 2010 at 9:15 am #

      Guys use oh i love you quote so that you would like it go. In your heart you already know the answer, you just don't want to confront it. I been through it before. He hasn't gotten over her. Best thing is to break up. If he really love you he wouldn't done what he had done to you. Unless he willing you change for you. You got to step your foot down.

  25. Pnai- July 28, 2010 at 3:07 am #

    i have ask my boyfriend all this question. specially number 1… he did tattoed my name but it was on his right wrist and i put his whole name on my left upper arm. I guess its finding the right guy to be with. its really hard now a days to find those kind of guys. but anyways i guess ur questions do work but my bf didnt run were still together and planning to get married in a year.. wish all the ladies out there all the good lucks!!

  26. lovemylife August 8, 2010 at 12:28 pm #

    Thats funny… i asked all of them to my boyfriend…. not seriously tho… but he's still right here… and as strong as ever.. he's alot more mature tho….21 yr difference with us…anyways…
    he wont get my name tatted, but he's getting my lips soon… at least i've got him branded… hahaha

    • Sumer24 August 10, 2010 at 4:17 pm #

      Love…i noticed that you and your bf have a 21 yr age difference…My bf and i are also distant in age…he is 18 yrs older. I've always had some issues with his personality but even more so lately..i was just wondering if you guys have communication issues and etc…for ex. sometimes i ask him questions that im interested in and he says 'you're not interested you're just being nosey'…and many more examples…

  27. chanti August 10, 2010 at 7:28 pm #

    ok this must be all American based questions

  28. Aneesacoleman101 August 12, 2010 at 2:17 am #

    LOLOLOOL this is really funny. the number one question is a HUGE no no both ways. i wouldnt want my name to be on my boyfriend's skin anyways. it seems kinda… stalkerish and obsessive

  29. LoveMe<3 September 18, 2010 at 5:17 am #

    shit i think hes cheatin nd weve been goin out since i was 12 nd im 17 now wat do i do>>>??

    • Luis,mylove<33 October 1, 2010 at 12:18 am #

      Ask him! tell him i want you to be completely honest with me are you cheating?? and if he says no trust him!! if you find out that he is leave him and dont turn back

  30. Joyce_gadin2000 October 14, 2010 at 2:46 am #

    I was looking for an advice about breaking up with my boyfriend

  31. Eddie Corbano December 17, 2010 at 10:17 am #

    Wow, someone really must’ve pissed you off, but it couldn’t have been this article, because it was written in an ironic sense of humor.

    Thank god most people get that.

  32. Cupcakee December 31, 2010 at 6:12 am #

    I’ve said alot of questions that I will say could have been far worse than some of those, and I’ve asked sevral of those questions before myself too, and My boyfriend is now my husband and he loves me more now than he did before cuz now he feels comfortable asking me anything.. cuz he is really honest, has nothign to hide and isnt ashamed of anythign with me cuz he isnt scared to ask, and neither was I.. its helped us be as amazing as we are now.. 🙂 and have wonderful children.. If he loves you, you canask him whatever and he wont run, but if your only playing around, he will run either that or you will, if you mean something to him, and he means something to you, he will stay by your side asking those questions right back to you 🙂 <3

  33. lee January 8, 2011 at 3:54 pm #

    I have to admit if I was a guy I would be running to if a woman would ask me these questions! lol

  34. Sierra Bell January 12, 2011 at 12:25 am #

    I know straight men that actually like shopping. Not everyone is the same. And us women can find the men that we share more in common with if we want to.

  35. ashleiallen January 17, 2011 at 4:10 am #

    i asked and he didn’t run hahahah

  36. Eddie Corbano March 10, 2011 at 3:37 pm #

    Thanks Franka :))) you made me blush.

    I’ll make sure my wife reads this ;).

  37. Eddie Corbano March 24, 2011 at 8:45 am #

    I know, thus the article was satirical :).

  38. lilmamma alreadytaken June 3, 2011 at 3:04 pm #

    mines does the same exact thing

  39. E-rad November 2, 2011 at 7:09 am #

    My boyfriend told me he can see me as his wife and that I’m “it” after two months of dating and wanted reassurence that I was on the same page. He said the L word first just btw. All men really are different.

  40. Eddie Corbano January 1, 2012 at 10:42 am #

    The question you have to ask yourself is: Can I live with his betrayal or not? (and of course: Will he do it again?).

    • Moira May 21, 2013 at 12:24 am #

      My boyfriend said “I love you” first. He “intends to put a ring on my finger. ” “Wants kids with me, I’m the woman of his dreams, wants to buy a home with me.” He backed out of everything. Still tells me he loves me and that I’m perfect. Now the line he gives me is “I feel like I’m not good enough for you”, and “do you feel like you are getting what you need from this relationship?” He is slowly breaking my heart. I feel extremely confused and angry. I feel that I should leave. It’s taking every last bit of courage and self respect to pack and leave. My heart is broken. I am a talented teacher. I am kind, passionate, caring, simple and tender, and beautiful. I wonder what I’ve done wrong, other than being a good person. It seems like that is not enough.

  41. Kaitlyn June 28, 2013 at 9:16 pm #

    He didnt run and he said he wants to marry me and get a tattoo of my name but in his neck and I’m going to get one of his name on my hip or somewhere down there.

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