How Long Should You Date Before You Seal the Deal???

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After my little debate about what women should wear to look hot with What Would Tyler Durden Do blogger Brendon last week, he emailed me bringing up a new topic of discussion…how long should you date before you seal the deal????

The answer to this question is simple…go with your instincts!!!  Do whatever feels right at the time. If u wanna give it up on the first date, then all the power to u LOL.  Chances are a guy wont judge, despite what some people might tell u.  As long as youre not the type of person that will be kicking yourself in the ass over it later then what the hell!  Why not?!? hahaha

Don’t do something just because you think youre supposed to.  Act based on how youre feeling.  If you want to go for it right then and there, then I say DO IT!  LOL.  But if it takes 5, 10 or even 15 dates, then that is absolutely ok too!!!!!! Every person is different and we all move at our own pace.  If a guy has a problem with that then chances are hes an idiot that you shouldn’t be dating anyway! ;)

Brendon of course had a quick response to my answer…check out what he had to say on WWTDD.com.

  1. Rapax says:

    I wish there was a little more spunk to these answers instead of these “please everybody” feel-good answers.

  2. Lil Bella says:

    That is so true take the risk cuz you never know …… How you been with the hole baby thing.. I hope yu doing ok.. Best wish’s too…. ToDay Is my Birthday i turm 18… I’m young….But I have lots of wish’s and one of them is to met you one day…..I hope you put some Pic’s Of how you are grow with the baby….. Thanks

  3. Fernanda says:

    heyyy…i agree!
    doesn´t matter time or any fuck…is just about LOVE!
    i hope u guys being happy with your family N the baby!
    congrats!
    =]

  4. Amber says:

    Kendra please please tell me where you got those darling shoes you wore the other day at ESPN The Magazine’s ESPY Style Studio. I want them!! Or at least what brand they are

  5. The Boy Who Couldn't Fly says:

    I don’t think putting out should hinge on the number of dates. I have a system that’s worked flawlessly for 5 years. I just get two receipts for everything I pay for on our date(s). I give one copy to her and keep the other.

    If I haven’t explored her nethers by the time the tab hits 80 bucks, I tell anyone who might possibly come into contact with her later in life that her p-word smelled like hot garbage and tasted faintly of buttermilk.

    But not before I give her what-for, “I could have gotten like 10 bee-jay’s down the street with the money I just shelled out on you. You’re like a 27 year old fifth-grader you backward-ass bitch. And I better not find out you tried to use those receipts come tax time!”

  6. Christina says:

    The Boy Who Couldn’t Fly,

    Get a real life. It is guys like you that give out VD’s like candy.

  7. jeff says:

    First off, Kendra is awesome.
    BUT, this idea of waiting 5, 10 or 15 dates is good advice for inexperienced young adults, allow me to share my opinion of how an adult should handle this.
    If you’ve gone on 3 or 4 dates and you still aren’t comfortable enough to have sex, move on (unless you are uber-religious or a virgin). I went out with a girl 5 times. We had fun. She enjoyed every date. She wanted more dates. But nothing was happening. No sex. Heck, no sexual contact. I never made it in to her apartment and she always had a reason not to come to mine. So I thought long and hard and realized the following:
    if you’ve gone out with someone more than 3 times and aren’t ready for ANY sexual contact whatsoever, something valid is keeping you from taking the relationship to a physical level. Be an adult and recognize that there may be a good reason you aren’t being physical with the person. Move on.
    When the girl called to schedule date #6, I explained to her that after 5 dates, we hadn’t done anything physical. That I recognized this as her being uncomfortable or unsure. We broke up. Now I’m no a-hole and don’t force anyone to do anything they don’t want to do, but in my 20+ years of dating, I’ve never gone out with anyone more than twice without any contact of a sexual nature.
    Don’t waste 10-15 dates. All you are doing is wasting someone’s time and costing them money, all while holding them back from seeing anyone else in the hopes that you will eventually show affection. Take your time to get to know someone, but understand that if you aren’t feeling sexually attracted to someone by date 5, you aren’t going to wake up one morning with a different attitude.
    I know many men who refuse to go on another date if by date 3 there hasn’t been any physical contact. Date 4 is surely going to be called off.
    In no way do I mean that you HAVE to have sex by date 3, but for an adult to wait 10-15 dates before any sexual contact occurs is a sign of insanity, virginity, religious belief, or immaturity.

  8. Christina says:

    It is a sad thing when people can count past one hand how many sexual partners they have had. Sex should be between to commited ADULTS. Yes, I’ve capitalized adults for a reason. I wasn’t yelling it, but emphysising a point. To me, and this is only my opinion, a sign if immaturity is the willingness to jump into someone’s bed you hardly know. 5 dates is not nearly long enough to know a person. If a man is unwilling to wait then he is no man for me.

    I am not saying that I condem anyone with Jeff’s opinon, to each his own on that one; however, I would not call it a waste of money if you have not had sex, unless that is all you are going out for. If so then go to this site call bootycall.com. Leave the serious dating for the rest of us.

  9. Jennifer says:

    I agree. My husband and I started dating March 2005, got engaged January 2006, and married August 2006. We were honestly going to wait till January 2008 but got married in August 2006 because he was deploying. We had a quicky. haha.

  10. Jennifer says:

    oh, haha, you were talking about sex. I look like an idiot. Our first time was 3 weeks into dating. We were each others first too :)

  11. Katster says:

    I love your answer to this Kendra. I feel like your attitude towards all things like this are very empowering to women and I commend you for that. Thanks for always speaking your mind… the majority of people in the public eye don’t.

    - Kat

  12. jeff says:

    It is a waste of money for two consenting adults to date 10-15 times before having sex.
    Unless, of course, you are the one taking advantage of the situation (read: women).
    Truth be told, dating ain’t free (though most women rarely, if ever, so much as offer to pick up a check).
    For the record: I only date women I find fascinating. I only go on more than one date if I am serious about the girl. If by date 5 she hasn’t realized that we are a good match, she won’t engage in any sexual contact and I decide to walk away.
    My 5 dates cost me close to $500. That same $500 is more than I spend on groceries for myself in a month. It’s more than I spend on my own entertainment in 3 months. It’s big money. And if the girl I’m dating isn’t in to me, so be it – no hard feelings. I am not one who hops into bed with any woman, but I’ll be damned if I’m going to spend $1000-$1500 waiting to see if she is into me.
    The thing many women can’t wrap their heads around is that when we go on a date and I end up paying every time, it becomes simple math. $100 per date should have some ROI. It isn’t about buying sex – it’s about something far less. If I’m going to spend money taking you out, I need to know you are interested in making the relationship into something more than some guy buying some girl dinner and drinks over and over. Don’t like it? Don’t date.
    I get that there are d-bags out there that think every girl they date should sleep with them. What I don’t understand is the idea that dudes should pay for everything and have to wait months to share sexually.
    Women use sex to get what they want. The few that don’t are the few that have sexual contact after a few dates.
    And for the record, I can count the number of sexual partners I’ve had on 2 hands. Because the number is 7. That doesn’t make me a bad person.
    My fiancee and I had sex on date 3 – is she a whore?
    The girl before her (whom I dated for 4 years) had sex with me on date 4.
    The girl before her (whom I dated for a year, was engaged, and then ended the relationship) had sex with me on date 2.
    The one before her (whom I dated for 8 years) had sex with me after our first date.
    I’ve been in several long term, fully committed relationships exclusively. Of the girls who refused all contact of a sexual nature past date 5, not one ended up in any sort of relationship with me past 2 months. So which method do YOU think works best?
    I am certainly not condoning jumping into bed with every guy who takes you out more than once. I AM saying that any girl that refuses all sexual contact after 5 dates or so is either religious, a virigin, inexperienced, or has major hangups.
    You want to know how men think? I’ve just laid it out.
    Don’t like it? Lesbianism is cool too. Or, just meet your future virgin husband in church.

  13. marie says:

    that guys stupid he think 3 dates is ok thats fucked up iam a fan and iam happy 4 u good luck girl

  14. julie says:

    I think its really silly of women to expect men to date them for over 10 dates with no sex. Thats a lot of time to invest in someone who is going to be a SEX partner, not just a friend. There’s no way that anyone can form a truly intimate emotional bond with love with someone they haven’t bothered to explore the physical side of things. That’s why I don’t believe in the abstinence until marriage bullshit. Love and religion are NOT enough to make two people who are sexually incompatible stick together. And we’re not just talking about vaginal intercourse-there is rolling around, foreplay, mastrubation and oral you can engage in if you feel uncomfortable with the vagina penis thing. Oh, and the stupid more than 5 people you’ve slept with crap just makes you look, stupid and immature.

    The point is: Sex is powerful, relationships are fragile.

  15. The Boy Who Couldn't Fly says:

    To: Christina
    From: The Boy Who Couldn’t Fly

    “It is a sad thing when people can count past one hand how many sexual partners they have had…[jibber-jabber-floobdy-flabber]…If a man is unwilling to wait then he is no man for me.”

    Christina is 13 years old.

    P.S. Christina, about what I said earlier, I’m completely serious.

  16. The Boy Who Couldn't Fly says:

    To: Jeff 4:13 pm
    From: The Boy Who Couldn’t Fly

    You just nailed it my man. That was eloquently delivered and perfectly put. I’d really like to hear the counter argument.

    P.S. I’m drunk as shit, Jeff.

  17. If a person has those types of expectation from day one, they are going to dominate the relationship which is never a good thing. It’s a process of give and take and not an ultimatum.

  18. Loren says:

    Don’t listen to that asshole Kendra. He’s just a typical loser male who only thinks about his dick.

  19. Johanna says:

    OMG, you’re soooo right Kendra!!

  20. Cadia says:

    I just wanted to say that I love the top you’re wearing kendra it’s ADORABLE! From what I can see at least. As for dating I was back together with my husband for 12 days before he proposed….we had sex around that time and we were married 5 months after that. It’s been almost 2 years so I must’ve done something right.

    Congrats on your baby! I was due around Christmas last year it’s a fun time.

  21. vanessa says:

    i agree, it shouldn’t be a pressure thing and it doesn’t matter if it’s 2, 5 or 13 dates… whenever it feels right..
    by the way i have a first date tonight lol so let’s see how far that goes hahaha :)

  22. Memphis says:

    Kendra:

    you are so cool… i live in Mexico city and i see your program, i really want to be happy with Hank.

    kisses from Mexico!! ajua!!!!!!!

    when i drink a shot of tequila i remember you jajajajajaja!!!

  23. Antonella says:

    I think in my own experience that for a woman is better to wait until at least the 3rd date to have sex because a man is more interested in her if she shows she is not an “easy” person, he has more respect and they both can know better each other…moreover after sex, the woman is more involved than the man, so the man can have more “power on her”–Before sex it’s the opposite, SHE is the one who has more control on the situation. I have experienced it with my husband: he is very handsome and every girl was at his feet, once he asked me out , first of all, he didn’t pay all that money and then he was asking me sex at first date…well, we had a lot of fun talking (I was always a bit misterious about myself) and knowing each other, but at the end of the evening I didn’t have sex with him…he was disappointed…every girl would have been crazy happy in my place, instead I was like saying him NOOO!!! Well, he took it as a challenge, he asked me out more times and after almost 1 month we made it…it was perfect!! and he was very in love with me- in 1 1/2 year we got married ;) and he is not only handsome, also 4 yrs younger than me…!!! AND 1 advice: he didn’t need to “buy” me or pay me the hangh out, we had a great time in cheap things like walking in gardens or going swimming together, take life easy!!!

    REPLY TO HEF RIGHT : Do you live on the earth or where??? God created Mankind in different kind and colors, so what? Kendra and her hubby are beautiful and their baby will be God blessed, believe me! It isn’t a matter of MONEY, maybe YOUR LIFE is based only on that, while they are truly in LOVE- You should be ashamed of all the awful things you wrote and of you huge ignorance. We are all happy if you don’t watch the show because it doesn’t miss that much- The show is for respectful people who believe in LOVE and FAMILY, you just show to be a failed unhappy lonely person – take more care about yourself then! LOOSER

  24. Nicole says:

    Kendra, I love you and your show! BUT every time Amber (your friend/roommate?) comes on she is SO annoying that I have to change the channel. She is incredibly stupid. For some reason they have given her small five minute clips where she talks and we see her doing stuff….She has NO sense and it’s not enjoyable to watch….maybe it would be entertaining if she were actually hott, but she’s not. She’s fat, loud, and ugly. Please let’s see less of her and more of ANYONE else!

    Also, I hope you would totally disregard the prior comment from “HEF Right” as obviously he is an ignorant bastard. I mean come on “Hef Right” this is 2009!!!! Welcome to the 21st century! You should be ashamed of the nasty things you said. Who made you God to judge anyone? If you don’t like the show or the choices Kendra makes GET OFF HER WEBSITE!! Dumbass!!!

  25. The Boy Who Couldn't Fly says:

    Hef Was Right About You

    What an asshole.

    A: You type like a retarded quadraplegic (I’ll wait while you look that word up…take your time…come on, you can find it…no, the q section, man…I know, q kinda looks like a p…got it?). I’m going to assume that English is not your first language so I’ll basically give you a pass on that.

    B: The word choices, I’m not offended by either. I don’t think there are any bad words. I think there are reasons not to use certain words but that doesn’t mean the word is bad, just the way in which it was used.

    C. The intent behind the word choices does bother me. I can only imagine the shit people you and your family must surround yourselves with. You’re too fucking stupid to realize that you should hate people one at a time. I’m sure you’d be reticent (…take your time…it’s in the R section…) to talk like that to my face. And I’m fucking positive you wouldn’t say that shit to Hank Basket’s face for fear of being pounded into meat-toothpaste you fucking coward.

    I thought I was a prick.

    You’re the stupidest person I’ve ever shit on. I’d actually be impressed by that if you weren’t a worthless racist dickeater.

  26. Monica says:

    Kendraaa, I love your new house.Please,please can you send me pictures or copy of the plan, my husband and I are going to start building our house next year and I told him I want your house! I just love it.It is exactly what I want, pleeeease!!!! ;)

  27. Christina says:

    The Boy Who Couldn’t Fly,

    I am not 13 but is is nice to know your IQ, thanks. I am a 31 yr old, married, mother of two. I was raised a good Catholic girl by my grandparents. So, no I do not think of sex the same way a lot of you do who was raised differently.

    I do have to give you two thumbs up to what you said to Hef is right. I stand by your side on that.

  28. The Boy Who Couldn't Fly says:

    Christina

    I didn’t really think you were 13, sweetheart. And I don’t really give all my dates the receipts either, believe it or not. Although I did do it once out of pure rage because my date was so unimpressed with my apartment. I was all, “Well I want a fucking refund you mean-ass whore! I probably could afford a nicer place if it wasn’t for paycheck vampires like you! BITCH!”

    Also, thanks for being a cool enough person to see that there is a common ground for rational human beings, even on the internet, and it pretty much falls under the umbrella term Basic Human Decency.

    P. S. “I am not 13 but is is nice to know your IQ, thanks.” Maybe you’re not 13 years old, but your comeback sure is. OOOH! :)

  29. brittannnnyy. [: says:

    yeah girl, i totally agree! you’re so smart!

  30. matt says:

    I only have one thing to say:

    Nobody who has replied to this post should be having sex until you finish second grade grammar class and learn how to spell, punctuate, capitalize or be able to form a complete sentence. It scares the shit out of me that the next generation of our country’s leaders will have learned their English from text messaging. I get stoopidur evry time. i git on enternets/! What scares me even more than that? The fact that you people are copulating. Ebonics will be closer to English than the language that your unfortunate kids will be using.

    The Boy Who Couldn’t Fly says:
    “A: You type like a retarded quadraplegic (I’ll wait while you look that word up…take your time…come on, you can find it…no, the q section, man…I know, q kinda looks like a p…got it?). I’m going to assume that English is not your first language so I’ll basically give you a pass on that.”

    I suggest that you take your own advice and look up the correct spelling of a word before flaming someone else for their English skills. I won’t mention the rest of the errors in your grammar contained in that single paragraph (if that’s what you want to call it). You fail.

    And any douche bag that thinks they are owed sex for spending money on a date is just that… a douche. Not to mention shallow, narcissistic and just 100% uneducated on what women appreciate and get turned on by. I can tell you from experience that it is not how much money you spend that turns women on. If it is, they are shallow whores who don’t deserve a nickel out of my pocket or my time. You will have much better luck and a much stronger relationship if you find more creative ways to spend your dates. Try going out on a date without spending any money. It takes effort and creativity. What the fuck is creative about spending $100 at a restaurant on food that you’re just going to shit out 12 hours later?

  31. Mo says:

    How long it takes is variable because you need to feel comfortable, find out if the chemistry is there, make sure they aren’t a complete shitbag…stuff like that. Unless your dating them simply for the sex. If that’s the case don’t waste time and get on that ASAP.

    That being said I jumped my husband four dates in. The chemistry was/is amazing.

  32. The Boy Who Couldn't Fly says:

    Matt

    YO, Youse ryte dute.

    It is obvious that my grammar is the worst that has ever been posted on the internet. Anyone with half a brain who read one-third of the comments on Kendra Wilkinson’s blog post could see that I misspelled quadriplegic on Kendra Wilkinson’s blog post and I apologize for that. Truly. I was unforgivably wrong to commit a typo on Kendra Wilkinson’s blog post and now that you point it out, I realize that I should be crucified upside-down at the very minimum.

    After all, who among us hasn’t typed the word quadriplegic 800 times per day since they were born? How could I possibly get that word wrong and on Kendra Wilkinson’s blog post of all places? I mean it is spelled just like it sounds!? And how could I ever impugn the intelligence of the commentator’s on Kendra Wilkinson’s blog posts by assuming a conversational tone while writing on Kendra Wilkinson’s blog post?

    What right did I have to comment on Kendra Wilkinson’s blog post in the first place before spell checking each word I wrote on KENDRA FUCKING WILKINSON’S blog post? This post, of all Kendra Wilkinson’s blog posts, when weighed against all others, will probably go down in the record books as the most influential writing that has ever been published; Strunk and White’s Elements of Style included. I can’t tell you how embarrassed I am that I didn’t catch my error on Kendra Wilkinson’s blog post. I’m sorry, Matt. I’m so sorry. Especially to you, the starving, illiterate, unmotivated children of the world reading Kendra Wilkinson’s blog post right this moment. I never even gave you a chance to succeed in this world…

    You sir, are a hero and a savior. Thank you, from all of us, for single-handedly saving the world from the deadly plague that is misspelled words. If it weren’t for you, I would have never realized that I misspelled (according to your accusations on Kendra Wilkinson’s blog post) one word out of roughly 750 that I’ve typed on Kendra Wilkinson’s blog post and the audacity with which I proclaim my disdain for the language you love so dearly, revere and protect right here, on Kendra Wilkinson’s blog post.

    P.S. Usually, if you have only one thing to say, you can avoid the conjunction “and” with which you started your fourth paragraph (if you want to call it that).

    An English degree only qualifies you to be broke, brother. But with that eye for detail, you could certainly rise to the rank of Senior Grammarian to King Sleep and Eat, ruler of the Hobo dominions.

    There are plenty of smart bums out there, man. There are very few hard working ones. Next time, do your best to argue a point against me rather than shitting on the syntax of my, admittedly (in several earlier comments on Kendra Wilkinson’s blog posts), hastily thrown together drunken ravings.

  33. Samantha says:

    I think it all depends on the guy. Some guys will date a girl for 5 years and never pop the question. Other guys will pop the question after 6 months.

  34. Samantha says:

    OMG are you people seriously gonna go through her blog and spell check her?! That’s reeeeeally lame! Give her a break, if she wants to abbreviate things who cares. This isnt a spelling bee so get a life. Why are you even on here?

  35. Thunder says:

    I think you are right Kendra I completely agree with you!
    Also you look gorgeous in this picture! You and Hank look so Happy!

  36. krissy in kiwi land says:

    hey kendra!!yeah u are soooooo right!!
    im about to seal the deal!! and man it took us like almost 7 yrs to be togetha and now im gunna be with most amazing man!he has been there for me thru thick and thein and as a woman i too agree on what u said about this.hope u have had fun on ya honey moon and ur belly must be growing by now!!

  37. Jan Harvin says:

    Kendra – you’ve always been my fave of the “Girls Next Door.” You always act just like yourself; you never put on any airs. I’m so happy you met your soulmate, and I look forward to seeing pics of your beautiful baby!

  38. Jan Harvin says:

    Kendra – I’ve always liked you the best of all the girls on “Girls Next Door.” (However, I love them too!) I’m so happy you found your soulmate, and I look forward to seeing pics of your beautiful baby. Congrats. P.S. My oldest daughter was born on Dec 24th.

  39. Megan says:

    Kendra!!! You’re episode of Kendra was the BEST one yet!!! But I am sooooooo looking forward to next weeks episode! When you tell your mom & friends your pregnant! Can’t wait! I love you girl & congrats on your marriage & being a momma..soon!!!!!

  40. Bia Justus says:

    Beautiful as always! I love them, make a beautiful couple … I love your program on E! and hope to see for very long … not miss any episode and I have you as inspiration! Kendra I love you and wish all happiness in the world … because you deserve!!! I am here in Brazil and the translation from Portuguese into English is not the those things hahaha more love to short many people here in Brazil and I hope one day may even know it… kiss :*

  41. Tonia says:

    Congradulations on your “New Marriage” I know you have many years of Happiness coming your way. You are young and to have been Blessed as you have to experience what you have in life if wonderful and I’m Happy for you. Get ready for your little bundle of joy and being the mommy and “Wifey” as you said on tonights episode. Giel you were cooking and you will see many more of those days dinner party of not with having a husband. I’m not married but I have experienced quite a bit myself. I know you love your family but I think you letting your assisant go was a good idea. Family and business do not mix. You will find someone ontop of their business and who will be organized and get things togather for you. From Scheduling or your daily appointments to meals, home and etc. Much Love,Sucess and Happiness to you!

  42. Geon says:

    It’s a gut thing… go with how you feel, and if you aren’t sure then that should be a sign…

  43. Florencia says:

    Do what ever you want
    Kisses from Argentina!
    Love you!

  44. ellie says:

    kendra, i beg you. don’t respond to this guy anymore. he is a walking STD advertisement. and a ‘tard.

  45. Loren says:

    Guys relax, it’s the internet. Answer her question and be done with it.

  46. CaliforniaGirl says:

    All that men care about is sex! I think we should make them wait forever! And Never give it up to them!! LOL.

  47. Muffin says:

    You’re right Kendra. =)

    Oh btw, I made this little wallpaper for you with pictures from your photoshoot. I just thought you might wanted to see it:

    http://i358.photobucket.com/albums/oo26/MrsCrapmuffin/kendrabanner.jpg

    :*

  48. Christina says:

    To The Boy Who Couldn’t Fly,

    I cannot stand racists! I will always stand beside anyone against racisim. And nice comeback to my comeback. Had me laughing.

    To Matt,

    This is a blog. Even Kendra does not write with correct grammer or spelling. It is not cool to attack those whom choose not to be perfect. Not all of us are English majors.
    Now, with that being said… Thank you for what you said about sex.
    “Try going out on a date without spending any money. It takes effort and creativity. What the fuck is creative about spending $100 at a restaurant on food that you’re just going to shit out 12 hours later?” I couldn’t agree more.

    Christina

  49. rachel says:

    OH MY GOD you are one to talk! you seal the deal the FIRST night haha doooooont lie!

  50. leah says:

    i totally on what you said. Do what you feel is right.

  51. THINKIES says:

    There is only one time that’s right for first time sex with a new partner – and that is when you are BOTH ready. not date 1, date 3, date 5 – when it is what you both want!

    I have slept with guys on the first date and also waited weeks before jumping into bed (and of course there were many I stopped seeing before it got intimate)
    - the difference was how I felt with that person and neither choice should be judged – after all it is my body.

    To the pathetic little boys counting up the costs of your dates and working out when they “owe” you sex, I suggest you find yourself a hooker and negotiate your deal upfront! I am not at all shocked that you are single – are you dating these girls because you want to get to know them better or just because you want to get laid?

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