Does she think I’m ugly?
Is it because I don’t make enough money?
Was I not witty enough for her?
We’ve all been there. Maybe it was a cute blond chick who also dug salsa dancing. Perhaps you came across a sexy Venezuelan brunette that shared your passion for football. We’ve all sent out messages to girls we were totally into, only to spend days waiting for the reply that never came.
When a girl doesn’t respond to your message, it’s only natural to wonder why. After all, what is a girl you haven’t met but a blank slate, on which to throw your deepest desires and fears?
But when it comes to online dating, it’s best not to let your imagination get the better of you. That’s because the #1 reason women don’t respond to emails is actually quite simple…
…they just plain don’t feel like it.
If you’re a hot female on Match.com, your inbox is probably packed with messages upon messages from countless men; most of whom fall somewhere on the spectrum of lame, insecure, and needy.
Do you think you’d ‘feel like it’ if you were a woman that was being bombarded by boring emails? I think not.
That’s why we have female clients that pay us to weed out the losers for them. Life is hard being an attractive woman…
Fortunately, there’s an easy way to stand out from the crowd. The key, in your first email, is to think beyond just making her interested in you. You need to also think about making her interested in your message.
We talk a lot about crafting compelling emails that stimulate her imagination, rather than boring her with compliments, but that’s only half the story. You also need to make it easy for her to reply. In fact, you need to make it so freakin’ mindless, that she doesn’t even know she’s written you back until after she’s hit send.
No, we’re not talking about using some weird hypno-seduction technique. The trick is a lot simpler. In fact, it’s so simple we can use it on every email we send, and you should too:
Ask her a question!
That’s it! With a good question, you’re basically already writing the first part of her email for her. Now there’s no magic to this, there are simply two basic rules you need to follow:
A good question should be both easy and entertaining to respond to.
By easy we mean that you shouldn’t make her think too hard. While girls like smart guys with a sense of humor, one of the dangers of asking a question that is too witty/thought out is that she will feel she’s not funny or smart enough to come up with a worthy response. Unless she’s head over heels into you, she’s only gonna sit there for a few seconds thinking about it before she says ‘next’ and moves on to the next potential suitor.
Asking that hot Latin dance fanatic, “what are your top 3 favorite Samba artists and why?” might make you feel smart, but it could make her feel stupid. Worse, it could look like you’re trying too hard, which is a HUGE turnoff.
By entertaining we mean that your question should stimulate her imagination in a way that makes her WANT to respond. A big problem with the questions guys typically ask on online dating sites, is that they don’t make women feel anything.
Questions like, “how was your weekend?” or, “seen any good movies lately?” do nothing to stimulate her imagination or emotions.
Alright, so enough with the bad stuff, how about a couple examples of good questions that have proven effective for us:
“So tell me…after a hard week at work, what would be your ideal weekend escape, from the moment you clock out on Friday, to the instant your head hits the pillow Sunday night?”
Or how about this:
“So that’s what your friends say about you…interesting. But what I want to know is…what do your enemies say?” (If her profile says that her friends say that she’s fun, outgoing, and intelligent, then write “So you’re friends would say that you’re fun, outgoing and intelligent… that’s great. But what I want to know is… what would your enemies say?”)
Can you understand why these questions work? Do you see how they stimulate imagination and emotion, rather than appeal to logic and reason? Do you see how they don’t make it too hard for her to respond?
Now there’s one last thing we should mention here, in addition to making your question fun and easy, you also need to ‘frame’ your question with ‘lead-in text’ so that it sounds RELEVANT. Make it relate in some way to what you say in your email, or to what she says in her profile. Otherwise you’ll come off as totally random and she won’t know what to make of it.
Plus randomness stopped being cute in middle school.
Grapefruit.
See 
Wow, this is one of the best articles I’ve seen on opening messages. Of course we all know that you need to watch your grammar and stay away from crude comments, but I often have a hard time telling readers exactly what they should say to get noticed. I have always advised them to ask questions to get a conversation rolling, but I love your advice on how to ask a well-crafted question.
Hi Lila, thanks for the positive comment, and linking to us on your blog! A well-crafted question is SO vital to starting a conversation, and can really make you stand out among all of the boring emails like “hi beautiful, what’s your name?” or “hey there, how are you today?”. We’ve got a small arsenal of highly-effective questions that we use for our clients. One of them got us a response just this afternoon with both of the following comments within the very same email “Your question is very interesting and unique.” … (later down in same email->)… “In my book, you get points for: asking me a creative question,”. Her response to our short but thoughtful message was 375 words long, and as interest level and the number of characters in an email are often directly related, it looks very promising that this will turn into an in-person date soon. Anyway, we have some great posts coming up soon and I’d love to hear more from you. Stay tuned
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cool, its been not too easy to keep a conversation, ya know. i mean keeping a girl responding to whatever move you make. so yeah, thanks for this blog
You should do the same in real life, and you’ll meet more girls that way. But you’ll also realise women have no communication or social skills. You’re doing everything, being witty and clever, and most women are too cowardly or conceited to even try to start being engaging–much less show they are interested.
So, my question is, when they don’t ask you any questions back and they’re not stimulating you by asking you how your weekend was, how many days before you hit the “next” button? I do what “The Rules” tell me and that is sitting back, waiting for a guy to email me. When he does email, I do what “the Rules” tell me and answer his questions, not going to their profile for “conversational” pieces, then the communication lays stagnant because I haven’t done anything to keep the conversation going. Please help a girl and tell me how long before I toss in the towel? Thanks!
Kristin, first of all, email guys. Settling for the ones that email you is just a bad online dating strategy. Of course you may get some winners in there, but why not take a proactive approach and reach out to some men whose profiles really capture your interest? Women email our male clients first all the time, and when we work with female clients, we do a ton of outreach to men that haven’t yet shown interest.
If you like a guy online and want to meet him, you should always add to the conversation. Give thoughtful replies to his questions and come up with interesting ones to ask him. A girl that only responds to your questions and nothing more can come off as very boring online.
But when you’re actually contributing to the conversation and he’s so boring that you feel like he can’t even hold up his half of the convo, just “next” him. If he doesn’t have anything interesting to say online, it will often be just as painful in person. And there are plenty of other options online, especially if you are doing more than just sitting back waiting for them to find you
This is what frustrates me . . . at the end of the article it says that these questions should appeal to emotion and make her feel something, rather than appeal to logic and reason. I’m not disparaging emotion here . . . all I want to say is that emotion and logic/reason shouldn’t be divorced and treated as if they’re in two different, hermetically-sealed spheres. Logic and reason is indispensable in any decision, and if the average woman’s only criterion for determining interest in a guy is emotion, then I guess I’m doomed to failure with women because I refuse to part with logic and reason. I do have emotions and I feel acutely (why else would I try and seek out a relationship?), but it is important to think things through as well.
Jeff, you make some good points… and if I’m understanding it all correctly, then my advice would be not to try to over-analyze things online. It’s hard to really get to know a woman better from behind a computer screen. Get to the more serious, logical questions when you have her in person, because until then, nothing is real anyways. Take things offline as quickly as you can, and figure the rest out in person. When you meet up, just be sure that you don’t kill her with all the boring, logic-based interview questions that men tend to ask on the first date… using them sparingly to screen her and frame yourself as a selective man can work to your advantage, but asking tons of them to ‘get to know her better’ will only bore her.
Thanks for the advice. I think the thing with me is that I like to go on dates with women that I have a general knowledge of and whom I already like. I’ve realized that this isn’t really how you play the game if you get involved with the “dating scene,” I guess . . . for most people, it’s something fun to do, and if you meet someone you like along the way, then great. However, being an introvert, I really don’t find dating for the sake of dating fun, and really don’t want to have to go on a myriad number of dates to finally light upon those few that you could potentially like. I’d rather go do other fun stuff, like skiing, biking, hunting/fishing, etc., etc., and meet women that way (that is, if they’re out doing those things, of course).