How to Message a Woman Again Even if She Didn't Reply to Your First Message

Hi Em,
Most of my messages have the attributes you discussed in your articles on messaging. So my question is, if I don’t get a reply, is there any follow up message that might trigger a reply? Or is it a dead issue?
Thanks,
Ben

Thanks for your question, Ben!  Lots of guys are curious about this.  The short answer is: it depends.  

First, decide if it's a good use of your time and effort to message someone a woman a second time when she didn't reply to your first effort.  Then, write a message she can't ignore.  Here's how:

1) Double-check that the two of you are a good fit on a basic level

A woman's profile is filled with important clues that suggest whether or not she might message you back.  Some things we'll never know -- like if she has a "type" or if she just started seeing someone else.  But there are a few details in a woman's profile that can tell you if there's a chance she might not respond.  Go to her profile and look for:

Your Match % 

Here’s the rule of thumb: 70% Match or more? Go for it. Less than 70%? Proceed with caution.

A low Match % can be an immediate disqualifier. If it’s lower than 70%, this usually points to serious differences in values, politics, religion, lifestyle habits, etc. These things matter when you’re looking to enjoy someone’s company for the long term. 

A low Match % is a useful red flag for you – don’t waste your time on this girl! – and women use it the same way. We look at this number as a quick way to ID and delete the guys who probably messaged us based on looks, rather than being a good fit in the areas that are important. 

Differences in Lifestyle & Values

Is one of you a smoker while the other is not?  How about opposite habits in drinking or drug use?  What about your politics or religion?  Does she want kids while you don't?  Again, big differences in your values or lifestyle could be the reason why she did not reply to the first message.

Distance

In general, we want to meet someone who is close-by.  If you’re OK with long-distance, or even just driving 1+ hours to see her, know that she might not be willing to do the same. If you want to message her anyway, make sure your message will make her see what she stands to gain by replying! 

Age Range

You know what age range you're looking for, but you also need to confirm that you’re within the age range that she’s looking for. If you’re 2-3 years outside the age bracket she specified, proceed with caution. If a guy’s more than 5 years out, she’ll probably ignore his message completely.

Height

While some girls don’t mind being taller than guys, other girls are bothered by this. Avoid a height difference of more than 1-2”. 

2) Review your own first message and profile. Would you message you back?

Whether or not you wrote a great first message will impact her desire to reply to your second message.

Check out what you wrote to her initially. Did you make an effort in your first message to start the conversation other guys can't?  Did you find common ground in her profile and ask her a question about something she said that was interesting to you?  Did you genuinely try to start a conversation by being curious about her thoughts, opinions, life choices, or passions? 

Then, take a look at your own profile.  Do you need to share more about yourself so that SHE can see that you're a good fit for her?  Check out this article on how to write a great online dating profile to make sure you're doing yourself justice.

3) Decide to write a great second message.

You're up against plenty of guys who have disregarded the basic details of her profile and wrote lazy first messages.  In order to stand apart from these more selfish men, you have to make it clear you're contacting her again thoughtfully and for good reason.

Make a Personal Connection

You need to make the connection for her to show her you're thoughtful and truly a good match.  Check out her profile to find something that is important to her, which you connect on.  Don't choose the easy route the second time around.

For example, maybe her profile says, "I have a weakness for people who make me laugh, who will volunteer with me, and believe in giving back."

Let's say you connect with all of what she's saying.  The easy route here is to go for the "make me laugh" strategy.  Guys who want to make a minimal effort will message her with a joke, or worse -- just tell her that they also believe humor is essential in life.  Anyone could do either of these things, but neither will help you make a personal connection with her showing how and why your values align.

On the flip side, you could make an effort to connect with her thoughtfully. Start by recognizing why she may not have replied to your first message and then start a conversation.  That message could look like:

"I realize Eugene is a bit farther than you wanted to travel out of Portland, but we have a few important things in common so I thought I'd reach out one more time. Volunteering has been a big part of my life, and I see that it is in your life also. (Then, say one short thing about why you believe it's important to you...Then ask a question about why this is for her, what it means to her, etc.)"

Be brief and polite, but be very thoughtful and make it clear that you're not simply messaging her again based on looks only!  

Always, Always Ask a Question

If you're emailing a second time, it's also absolutely critical that you attempt to begin a conversation that asks for her thoughts or opinions with a question that requires more than a yes/no response. 

A great trick to asking questions that get to deeper sharing and prove you're interested in her thoughts, feelings, and opinions, is to ask "why," "what," and "how?"  These ask for more than a yes/no answer, and dig much deeper than asking how someone's weekend was spent.  When you ask questions like these, you'll start a conversation that proves you want to get to know her -- and whatever makes her who she is.

So many men ask shallow questions that don't show an interest in a woman's thoughts, opinions, or the reasons WHY she enjoys her hobbies, job, or doing the things she loves.  It's usually an indicator that they didn't really read her profile or don't care about much other than her looks!  But when YOU ask a question that shows you read what she wrote, found it interesting, and want to know more about WHY she gets excited about certain things, or what motivates her -- then that's really flattering.  You'll really stand out from other men when you prove you can do that.  

Asking questions like these are critical in the first (or second) message, and as you continue the conversation -- before asking her out.  This will be engaging for her -- and she'll feel more comfortable that you're truly interested in her for all she has to offer, not just a physical connection.  

3) Hit Send & Let it Go

If it works, fantastic!  Continue to lead the conversation in a way that helps you both learn about the other.  By the time you get to the first date, you'll have so much to talk about, it'll be more fun and less awkward for both of you.

If it does not work, then at least you know you did your best to show her the genuine connection you two might have, and that she may have her own reason for not responding.  Maybe she likes guys with beards, or blond guys, or some other random preference!  Love is a funny thing, and if this one is not the partner you're looking for, you can bet she's on her way to you. Get back out there and find her!

READ MORE Tips for Messaging