12 Guaranteed Rules for a Great Date

I give good date. 

Call me arrogant, call me conceited, call me Slappy the Half-Brained Clown.

 12 Guaranteed Rules to Great Dating

I call it confidence.  I’ve never been turned down for a 2nd date, and in general I’ve never had trouble meeting women who were interested in dating me.

Wanna know why?

It has nothing to do with having game, being stunningly good looking, or having a huge reproductive organ. (I’m not confirming or denying the existence of any of those things!)

There are 2 reasons for this:

  1. I am extremely picky with the women I go out with
  2. I pay attention

It’s really just that simple.

But ToBlogOr – if it was really that simple, why doesn’t everyone do it?

Good question. You wanna know why? Because we’re too self absorbed.

I’m a recovering only child, but a long time ago I started to understand the power of paying attention. Remembering little things started to get me places. It helped me succeed in my career. I had problems dating though. The moment I started applying the same principles to dating, all of a sudden I was an extremely caring guy that all the women wanted.

What??? Really?


My plan for today was to provide a list of the 12 Guaranteed Rules to Great Dating – but you know what? There are really a lot more than 12, and they are really more like guidelines. The majority of these apply to both men and women equally, and I’ll include a couple of extra at the end for men and women

So let’s go!

The 12+ Guaranteed Rules of a Great Date


Don’t be a bore, make your date soar!

The more interactive your date is, the better. Something that involves laughter is always important. Guys – chicks dig guys that make them laugh. If you aren’t funny, do something that involves laughter.  Suck up your pride and try something you haven’t done before, it’s ok to laugh at yourself.  I went on an ice skating date once and fell on my ass so many times that I think it’s now permanently flat.  You know what though?  The girl thought it was really endearing.  We couldn’t stop laughing.

Don’t be a pretentious prick

Dating is not about being impressive. Dating is about being YOU. Have enough confidence in yourself to BE yourself. If you are having some self confidence issues, then just be glad you aren’t this guy:

12 Guaranteed Rules To a Great Date

Dress to impress

When I said to not be pretentious, I didn’t mean don’t look good. I’m a big fan of over-dressing slightly.  No full tuxedo for a fast-food run.  If you aren’t sure if you should wear jeans or slacks — go with slacks. If you aren’t sure if slacks or a suit. Go with a suit. My one corollary: If you aren’t sure if you should go with tighty whities or commando — definitely go commando.

Pretend you are Obama

Now, with your huge pretend ears…. LISTEN TO YOUR GODDAMN DATE!  Don’t just hear him/her talk – ask questions.  Engaging questions.  Open ended questions.  If you don’t care what they have to say…. PRETEND. 

Dating Hint: After your date, write down some of the things you talked about and review them before you talk to your date the next time.  As an example, take a note about their brother’s impending graduation…. and then ask them about it next time.  I couldn’t give a rat’s ass if you care about their brother, but it shows that you listened!  Trust me, this one never fails.

Everyone hates a mime

I hate it when my date only gives me 1 or 2 word answers to my questions.  It makes it sound like they either 1: don’t like me or 2: are stupid.  You goal is to be talking 45% of the date.  You want your date to be talking just a bit more than you, and if things start to get off kilter, right the ship! 

12 Guaranteed Rules To a Great Date

Buy a fricken watch

Be on time, wouldja?  If you aren’t going to be on time, let your date know.  Ok?  I HATE waiting for people, because I hate being late.  I like to plan.  I know that not everyone is like that, but how well do you really know your date?  Not very – so do us a favor, and be on time.  It shows us that you care.

Surprise surprise surprise!

Ok so I already talked about listening and taking notes – here’s another way to put it to use.  One of my signature moves is to bring a surprise on a 2nd or 3rd date.  Nothing expensive, just a little small thoughtful gesture.  Women almost always appreciate flowers, but I like to take it a step further.  Before our first date, GF and I had a conversation where she  told me about how she loved the song Sexy Back, but didn’t have the CD.  I hadn’t even heard the song, but I went out to a store, bought the CD, and then surprised her with it on our way to dinner.  Trust me, this stuff works.

Don’t do the friend pat

Touch a woman like she’s a woman, not your buddy.  Don’t pat them on the back or shoulder like a friend would do.  This is called the “friend pat.”  This is highly offensive to women, so don’t do it.  There are a good number of good ways to do it.  Women?  Touching a man is always sexy, just understand that if you start touching us a lot, we think we’re gonna get some. 



Dating Tip:  Men – if you aren’t sure what to do at the end of the night, give her a kiss on the cheek.  You can’t go wrong with this, women think it’s cute…. just make sure you aim appropriately.  If you give her an obvious sign that you are going in for just the cheek, she won’t flinch.  If she wants more, she’ll turn her head.

Friend Pat!

Warning: Friend Pat!



Thank you Jesus!

If someone took you on a great date – is it too much ask you to write a quick thank you note?  In fact, even if you TOOK someone on a great date, it’s ok to send them a thank you note too!  People love appreciation.

Hey, nice ass!

People love to be complimented, women especially.  If you think they look nice, tell them… and be specific.  Just remember, that you need to compliment them not the item of clothing.  I’ll give you a couple examples:

Bad: Wow, that’s a great dress!

Good: Wow, you look great in that dress! 

Bad: I really love your earrings.

Worse: Those earrings really go great with your dress! (No straight man says something like that)

Good:  Wow, you look great – I love your earrings!

Bad: Those jeans make your ass look great.

Good: You have a great ass.

Clean your car, get gas, etc

Dates should never include chores.  Chores are what you do in your free time.  Be prepared: if you are driving, clean your car out ahead of time, get gas, and know exactly where you are going.  Women: the last thing I want to do when I’m on a date is go to CVS with her to buy tampons.  So do yourself a favor, and plan ahead.

Don’t play the 1 up game

This is a game only assholes play.  Be impressed with your date, they like to feel like they are number 1.  All 1 upping does is makes them feel like they aren’t good enough.  If you make it farther than this date, you’ll have time to tell your story eventually.  In the meantime, be more into them than into yourself.

Don’t be a douchebag

Sarcasm sucks.  Period.  Keep it out of your first dates.  No one wins when you are sarcastic.  It’s offensive, it isn’t funny, it doesn’t belong in dating.  You don’t know them that well, they don’t know you that well…. and trust me, it won’t get you anywhere.  Just don’t be a douche bag ok?

 12 Guaranteed Rules to a Great Date

Ok, so I’ve now provided you with all the rules that guarantee you will have a great date (assuming your date isn’t like the guy above).

Post Date Tip

Your date is not Ellis Island

Don’t be needy and desperate.  You are dating, you aren’t married.  Be cool.  Be relaxed.  If you seem desperate and needy, people won’t like dating you.  This means sucking it up and not over-communicating.  If you haven’t gotten a response back from your text earlier…  Suck it up.  Your date has a life of their own.  If you haven’t heard back, wait at least 24 hours and then follow up.  If you still don’t get a response, you are only allocated 1 last call…. so use it wisely.  Anything more than that is an annoyance.  If they like you, they’ll get back to you eventually…. if not? No loss – move on! 

Are we done yet?

No! Because we have to cover both sides of the issue.

How to get out of a bad date

If you are on a bad date, and want to know how to get out – go here. The website also includes helpful tips for situations such as: “How to Survive If You Wake Up Next to Someone Whose Name You Don’t Remember” and “How to Determine If Your Date Is an Axe Murderer”

I’ll be reporting live from London tomorrow – so stay tuned for some Greenwich Mean Time Dating Tips!


15 responses to “12 Guaranteed Rules for a Great Date

  1. Great post — the 1 up crap pisses me off to no end. Also name dropping – I could care less if your brother is married to the VP of someone fabulous company or your pet goat worked in the White House – sigh.

    If you know your date is into purses and shoes – comment on those too……..like great shoes.

    I notice men’s shoes a lot!

    Awesome post – you should get a book deal for this.

    Thanks! Yes, I’m with you on the name dropping. Sheeeeesh! I hate that.

    Book deal? That would be awesome – I could quit my job and just bitch for a living! What a deal!

  2. I have to take the Friend Pat ONE STEP further.

    You probably won’t even believe this, even if you have completely recapped on my awful date of last night, because I left it out.

    We were standing, waiting to be seated before dinner last night. I said something funny, and I SWEAR TO GOD, my date reached over and poked my belly.

    Finger to the stomach. Pillsbury Dough Boy style.

    Not that I’m flabby. I’m not. But I couldn’t believe that his physical response would be to poke my belly.

    NEVER do this to a woman.

    There you go. Worse than the Friend Pat.

    Way to 1 up me, lucky we’re not on a date eh? Ha ha Yes. You are totally right, that is much worse. I am continually amazed by the things that people do on dates. In my lists I try not to put things that would be obvious for those of us who own more than 1 brain cell. Apparently I underestimate the stupidity of some people though, eh? Wow.

  3. Never greet a blind date with a handshake on the first date. This is AWFUL. No we have not “met” yet, but this is also not a business arrangement. A hug or peck on the cheek, or even no first contact is all better than a handshake.

    Hmmmm I have to think about this one. I’m not sure if I agree or disagree. I’m a guy so I like a handshake – you’re right that its not a business arrangement, but since I don’t know the person at all, I would feel awkward giving them a hug or a peck. There’s a level of intimacy that is needed for me to feel comfortable doing that. I might have to go with the no-contact thing then. I’d be interested to know how other women feel about this.

  4. I never would have thought about sending a thank you note. I do though if it was a good date the next day send a quick text saying I had a good time.

    I think for the first date a text is ok, a call might be a bit much for some men and they might think you are being needy.

    Good point. When I think of thank you “note” – an email is fine, and a text is marginally acceptable, unless you really didn’t have that good of a time. I agree with you – I wouldn’t do a call… it’s all about putting it in writing. People so infrequently write thank you notes these days that it’s almost a shock when you get one.

  5. You’re arrogant, conceited, and Slappy the Half-Brained Clown.

    What? You said to.

    You’re welcome.

    Thank you for following directions well. Now if you only followed my directions that well ALL the time, I might be able to make one of your blogger happy hours 😉

  6. See, I think a warm handshake is ok on a blind date. I don’t want people all up in my biz right away. That happens after a few hours and a handful of drinks.

    You “nice ass” point is perfection.

    But what if we want to “be all up in your biz?” heh heh I agree – there are different kinds of handshakes – theres a business one, and then there’s a warm one (hmm maybe this is a blog entry in the making??). I can’t stand people who hug me that I haven’t met before.

  7. Oh, DON’T be a douchebag. Damn it all…

    Yeah, sorry about that one dude. I guess it’s lucky you have a gf then, eh?

  8. Dude, I know you did not write here, on this blog, that after a date you do a postmortem and make post-it notes so you have talking points for the next date. Wow. I bow to the master.

    You know, I was *just* telling someone today that Mr. SingLikeSassy didn’t kiss me until our fourth date and we had all this chemistry but I was starting to think I had read the situation all wrong and had my girlfriends all trying to figure it out and then, he kissed me. And it was wonDERful. Siggghhhh… :::swooning:::

    Haha I wrote it! You know why? Cause I have the short term memory of a fruit fly. If I don’t write these things down, I forget em. It’s not like I take copious notes – I just write down 3 or 4 important points I want to remember.

    4th date eh? Wow – go him. I guess it worked out eh?

  9. Spot on about the sarcasm… I’ve watched/heard dates crash and burn because of that

    And when they do it, it’s almost like they don’t know when to stop. It keeps going and going and going like a huge sarcasm snowball.

  10. Be yourself. Do not pretend to be someone else.
    Do not bore your date or else you’ll never see them again.

    Nice Post

  11. Love this.

    My personal first-date dealbreakers are as follows:

    Being rude to the wait/bar staff and/or not tipping well.


    Thanks. I agree, and if you are getting motorboated on the first date, well, heh, you might want to reconsider the kind of guys you are going out with. I usually save that for, at a minimum, the 3rd date.

  12. Second SingleGirl- NOTHING worse than the Pillsbury-poke in the stomach. NOTHING.

    Also, I’m with CH- a handshake is weird and formal. The half-hug, possible kiss-on-the-cheek will work just fine, thanks.



    Per the above comment about handshakes: I’ll shake someone’s hand, and I don’t have a problem with it. I was kissed on the cheek for the first time just recently (it was the first date), and I was a little surprised by that. It wasn’t bad, just unexpected.

    Sorry, I should have checked with you before posting his pic. My bad.

    Hand kissing? Nice – that’s a bit old school! I appreciate that!

  14. Great Post.

    I love the rule:”Don’t be a pretentious prick”,
    its right.Dont pretend to be another person, act as who you really are.


  15. Our first date went really well, he did everything right and it was great but he must’ve spent a fortune paying for it all. Should I offer to pay next time or do guys get offended by that?

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