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Gentleman’s Guide to Online Dating

Online Dating Openers


These openers are divided into several different categories.

• CLASSY/SIMPLE openers are most appealing to older women, or those with serious
profiles that communicate their intentions (i.e. “I’m looking for a serious relationship…”,
“I’m tired of the dating scene…”, etc). They’re also useful for men who are either a bit
more distinguished or don’t have a personality that would fit with the more juvenile or
humorous openers.

• FUNNY openers work for most women, and are a good go to for women that you think
get quite a few messages. They will stand out and communicate a bit of personality.

• KAMIKAZE openers are risky but get the highest amount of interest if successful. They
land less often than the other categories but work very well when they do land, and will
be great for those who have a very nonchalant approach to dating sites.

• FOOT IN THE DOOR openers do things like feign familiarity or create false backstories
in order to “trick” the women into replying. They can work better than others in terms of
getting a reply, but require strong follow ups to keep her interested.

You can use these openers as they are, but try to see them as templates and make an effort to use
your own.

Classy/Simple Openers
“You’re cute and I like your profile, you’re not a scientologist are you?”

“You must hear it a hundred times a day, but I think you’re beautiful and you should hear it more.
(Random personalised question*)?”

*Random personalised questions can be things either from her profile, ie “Have you ever
surfed up in Tofino?” (If interest in surfing on her profile) or something more random ie
“Hmmm you have a creative look, do you paint?”

“You seem fun. You’re totally the kind of person that I’d go down to the beach, drink a box of
wine and laugh all night with.”

“I’m never on this site, pretty much set it up as a joke, I’m not going to send you a funny joke or
clever bullshit line but I will be honest: You’re fucking GORGEOUS and interesting, so I want to
talk to you. Send me your number and I’ll call you, OR reply to this and let me convince you, but
I’m not sure how long I’ll be on here.”

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Gentleman’s Guide to Online Dating

Funny Openers
“You’re adorable, is it too forward to say we should get married and have a hundred kids together?
Hint: It doesn’t matter.”

“‘LOL, me and my friends are talking about you.” (Credit: Labyrinth)

“HEY did you know that your Boyfriend is GAY!”


(And for half-kamikaze you could follow with...)
“Your face is sexy and your arse is OK ;)” (Credit: Labyrinth)

“Hey, I’m going to be honest. I’m going to an 80’s themed party and you’re the most 80’s looking
woman I’ve ever seen. I Bet everything you put on immediately turns acid washed. You’ve met
your match, and we need to make this happen. Free booze.*”

*Adding “free booze” to the end of any message seems to increase replies. Also this party
doesn’t have to actually happen, you can always say, “Well I have to make sure you’re
normal first!”

“You look really familiar…you don’t play world of warcraft do you?”

This one is a bit of a kamikaze in that she’d need to either be a gaming chick or internet
savvy to get the joke. You could follow up the roleplay by talking about how you’re a
celebrity on WoW and it’s kind of a big deal.

“I was thinking of selling all my belongings buying a hovercraft and fleeing town wearing a
tuxedo on wednesday. I’ll need a classy/sexy lady by my side to complete the look. Are you in?
Free Champagne.”

*See above about mentioning free liquor.

Kamikaze Openers
“Hey this might sound weird, but I’m a musician and after I read your profile I decided to write
an entire album based off of it. I just finished it, it’s called “They only come out at night.” Google
it! That’s me on the album cover. Sup?“

“Look, I know I broke your heart, and I’m sorry. Believe me, I spend every night regretting the
decisions I made all those years ago on that Moroccan camel adventure. You need to learn to
forgive me darling. I can’t go on like this, this is too much. God damn it I’ll give you Jeffrey back
if you’ll only see me, I hate that fucking monkey anyways!”

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Gentleman’s Guide to Online Dating

Foot in the Door Openers


“HEY! I totally met you at Mike’s party a while back! We talked about (obscure tv show or band
from her childhood) and did JELLO shots. You had the filthiest mouth of anyone I’ve ever met, I
Can’t believe I found you on here, how have you been doing!?”

“Sorry about that last message, a jealous friend of mine got a hold of my computer and sent
nasty stuff to all the cute women on my match list/area/favourites. You’re cute so you get one free
punch redeemable anytime you happen to see me. No questions asked.”

“I’m pretty sure I saw you downtown today running down the street holding what I believe to be
a small dog in a hotdog costume, and laughing hysterically. What the hell was going on? Also
you’re cute.”

“Pretty sure I mud wrestled with you at a massive house party in (local residential area) last year.
I might be wrong but…we should go get some pudding or something sometime =)”

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