Online Dating Emails: How to Stand Out So You Get His Response

Woman writing online dating emails

Writing those online dating emails to men can be a living hell. But you already know that…you’re here reading this. Contacts via email are what actually lead to dates, sister. So, you must know how to do it to make that man sit up and take notice.

I know how frustrating it can be when you’re putting in the work online and not getting much in return. Maybe you’re emailing guys a lot but not getting any response. Maybe you’re sending flirts, clicking “like” or “meet me” hoping that he’ll take the hint and email you…but that’s not happening.

Thinking it’s his job/role to do all the work will get you nowhere fast when you’re using online dating to meet men. So, if you are not initiating, I highly recommend that you start…like now, OK?

Forget about “The Rules” crap and the idea that if you take the lead it will affect his manhood somehow. The online dating world is different than the outside world. Writing men the first email is not only fine, it’s necessary. All you are doing is reaching out and showing interest—not asking him for a date. Most men dig that.

Research from an OKcupid study shows that you are at an advantage when you reach out first because men tend to respond. Sometimes the simplest solutions are the most elegant, no? In fact, women are 2.5 times more likely to get a response than men if they initiate.

(A little side note here: these men have had to be the initiators and risk rejection for decades. For every “no” you’ve had, they have had 50+. That’s also true with online dating. So when you’re feeling down or rejected, keep this in mind. Perspective and compassion are powerful tools during your journey.)

Here’s the thing, there is a lot of competition out there—especially if you’re a woman dating after 40. Move into your 50s and 60s, and the competition can get fierce. (Unfortunate, but the truth.) Having a fantastic profile is a must, but coupling that with the art of writing emails sets you up to be a winner in the game of online dating…and finding love. (Like I did in 2006.)

Get Him Thinking About You

I was online for many years before I figured out the great-profile+great-email formula and met my husband on I will never forget how it felt to send an endless number of emails, only for them to end up in the pit of Internet rejection hell.

So whether you’re new to initiating messages to men or have been churning them out routinely, writing a star-quality email—one that stands out from the pack— is key to getting a response that could lead to a great date and much more.

Online Dating Email: It Can’t be Like Any Old Email, Right?

You want your email to stand out above all the others so that you are the one he wants to get to know better. I’m going to walk you through how to write an enticing, intriguing email—one that gets him thinking about you and one he can’t resist responding to.

So let’s start by taking a look at a typical email sent by the vast majority of women dating online. It goes something like this:

Hi, Bob. I like your profile, and it looks like we have a lot in common. I also love to travel and read mystery novels. Check out my profile, and if you’re interested, get in touch. – Susie

If Susie’s email is landing in the inbox of a relatively handsome 50 or 60-something man with a pretty good profile, chances are Susie isn’t getting a date. She’s may not even get him to read the damn thing.

A great email attracts, entices and begs to be opened. It makes him pick yours before Susie’s. It makes him smile and feel light. It piques his interest and tells him there’s more good stuff to learn. It makes him want to reach out for more.

The email that gets responses communicates a sliver of who you are and lets him see why you’re someone he might want to be with. It reveals something interesting about you and inspires him to start a conversation that leads to a date.

My Winning Email Writing Formula

Here’s my formula for writing emails when you’re dating online. There is certain finesse to writing these, but with some practice, you can master the craft. (I coach my clients how to do this all the time. After a while, they all get it. Practice makes perfect!) You don’t have to follow this exactly or have it in a certain order. Write it so it sounds like you, and so it shows YOUR PERSONALITY!

Here’s a BIG TIP: this isn’t anything like writing a business email so get that out of your mind. It’s more like writing to a girlfriend. Write like you talk. Be conversational. To practice, say out loud what you would say to him if you met him at a party.

1. A Spectacular Opening Line/Subject is Key

Make your opening line enticing, intriguing, or flirty…and personal. You can even get a bit provocative, but don’t overdo that or you may send an I-want-sex-and-you-can-count-on-it signal. (Unless that’s what you want, of course.)

Some sites do not have a place for a subject line. Usually, then the first characters of what you write show up in their inbox, so make your first sentence count!

2. Be Positive, Playful and Real

Be upbeat, positive, keep it light, make him smile. Don’t be afraid to share something about yourself that isn’t perfect. Show him you’re a real person. For instance, if you happened to have backed into a post today or spilled coffee all over yourself during a client meeting, tell him. And then tell him how you laughed about it! If you nailed a client you’ve been working on for months, tell him and that you celebrated.

If it’s your style then go for humor…always a good way to break the ice. But watch out for sarcasm, which does not translate well on paper. Be a little flirty but again, don’t overdo it. Flirty PS’s are good…leave him with a smile.

3. Be Original—Stand Out from the Pack

Stay away from what every other woman out there is going to say. Things like “your dog is so cute” or “I think it’s great that you read xyz” or “it’s wonderful that you volunteer…me too!” or “I’m looking for the same thing you’re looking for.” You know what it’s like to get emails that have no real meaning, right?

Instead, notice what seems important to him—his passions, values, dreams, how he envisions life in relationship — then riff off that. Share a little about yourself that complements him, but don’t just say it how everyone else does. (For more, see #6 below: Tell Him Something About Yourself.)

Have some fun with it! For instance, think food…yes food. Food can be fun and sensual. If there’s something in his profile about food—his love of ice cream, pasta, a certain ethic cuisine, whatever—if it speaks to you, comment on it. “I love ice cream too. Give me rocky road dripping down the side of a waffle cone and I’m one happy woman. What’s your favorite?” “I know what you mean about Italian food…reminds me of love and family.” You get the idea?

Don’t be afraid to talk about what you’re looking for relationship-wise, by the way. If he talks clearly about what he wants in a relationship and you agree, it’s good to share that with him. Let him know you’re looking for the same thing and how cool it will be when you find it.

(Another side note: if you’re looking for a lifetime partner or marriage, I recommend that you don’t prioritize contacting a man who doesn’t, in some small way, indicate his interest in a forever relationship.)

4. Give a Sincere Compliment

Everyone likes to be complimented, right? Do NOT waste words by saying that you like his profile. That’s a given. Keep it real and don’t make it totally forward or presumptuous. You seem amazing, or you’re incredibly smart is too much to say to someone you don’t even know. Make sure it is sincere and not over the top. (Or don’t include one at all.)

Many men are keen on compliments about something they’re doing: his work, an accomplishment or his character. A woman’s admiration/appreciation are often at the top of a man’s “must haves.” Something like “can it be true that you’ve figured out the mystery of balancing of work and play? Congratulations. I admit that I’m looking to do a little more play.” (Compliment with a little flirt thrown in.) “

Saying that you’d like to know more about something he’s interested in is a compliment too. Notice what his profession is and say something about it. If guy is passionate about music, skiing, sports…”Love your good taste in xyz. That’s a turn on for me too.”

Look at his photos…maybe you’ll see one or two that makes you want to know more about him: I hear you can tell a lot about a man by his golf game. Is that true?”

5. Show that He Evoked Emotion and Good Feeling in You

If you got a genuine kick out of reading his profile, or if something really resonates with you, tell him! “What you said about xyz made me smile/laugh out loud” or “Your picture of xyz is just beautiful/fascinating/hysterical” or “the way you describe xyz makes me feel xyz.”

I know this sounds like a no-brainer, but don’t waste time on profiles that don’t say much or don’t have something that triggers your interest. Let him know if he says something that moves you to genuinely compliment him, or inspires you in some way to know more about him.

6. Tell Him Something REAL About Yourself

Again, you don’t want to do the typical “I’m looking for the same thing you’re looking for.” That’s insincere and doesn’t create any emotion in him whatsoever. Instead, share a “nugget” or two about yourself. Don’t just tell him what you DO and point out shared interests…tell him a little about who you ARE.

Share a brief, juicy fun thing you did last weekend, what excites or delights you, what music gets you dancing, what makes you laugh. Help him get to know you and see some of your personality. Make him want to know more and go to your profile.

Here’s an article that’ll help you let a man see the kind, confident woman of depth that you are, rather than just deliver the same lines he hears from every woman.

7. Ask Him a Question

Make it easier to write back by asking him a question. Make it something open-ended (not a yes or no answer) but not too personal or deep that it requires a dissertation. Ask about something you care about to help you get to know him.

8. Tell Him Your First Name

I know that seems obvious, but many people forget this. It personalizes your message.

A Winning Email

Now all this doesn’t mean you send an email a mile long. The finesse comes by combining these to make a short, sweet contact with some yummy stuff in it. Here’s an example of a winning email.

Hi Fred5081,

I know about a lot of things, but a physicist I’m not. It would be fun learning more about the where’s and why’s of how matter and energy interact. (Ok, I admit…I looked that up. But my interest is real.) Or, if you prefer, we can just swap stories about our most embarrassing ski experiences. (I have several.)

Like you I love hosting parties. Last week friends were over for a poker party. I lost big time but the lasagna I made was a big hit. Good fun with good people.

I look forward to hearing from you. Enjoy the beautiful day.


PS: You said you need help digging your pond…sounds like fun to me! Can we jump in when we’re done?

Writing Online Emails – A Closer Look

Now let me break this down:

I know about a lot of things [nugget – tells him you’re confident, smart and proud of it], but a physicist I’m not [you’re smart yet humble and not interested in competing with him]. It would be fun learning more about the where’s and why’s of how matter and energy interact. [compliment and men love the thought of teaching us stuff.] (Ok, I admit…I looked that up. But my interest is real.) [a little humor and honesty, and shows an effort to learn about his interests. Only say something like this if it’s true!] Or, if you prefer, we can swap stories about our most embarrassing ski experiences. (I have several.) [response to something he mentioned; offers a lighter subject; a nugget that she skies; a little self-deprecation.]

Like you I love hosting friends. Last week friends were over for a poker party.  [shows compatibility and nuggets about yourself ] I lost big time. [a little bit of self-effacing is good] but the lasagna I made was a big hit. Good fun with good people. [she shows she’s a cook; appreciates her relationships; and a good sport!] 

In two weeks I’m going to Prague and on a riverboat cruise. [nugget and compatibility] I’m so excited! How about you? What’s coming up that’s exciting in your life?[kinda easy question to answer and gives you info you want to know]

I look forward to hearing from you. [confidence instead of “hope to hear from you”, but you’re not asking him out, either.] Enjoy the beautiful day. [upbeat, positive sign off.]


PS: You said you need help digging your pond…sounds like fun to me! Can we jump in when we’re done? [light; flirty, positive; nugget that she enjoys being active]

This email is a little long, but I wanted to show you an example of how the formula can work in an email. Also, in this case, his profile was somewhat long, so we matched his content. (Yes, this was a real email. Karen did receive a response from Fred and had a few dates with him. Now she’s living with her life partner who, by the way, she met online after writing him an email!)


I want you to have realistic expectations. Regardless of how awesome your profile and message, you may only receive a small percentage of responses. There are a hundred reasons why a man won’t write you back, and 999 of them have nothing to do with you as a woman. Remember that you only need ONE!

Start writing these winning emails and you’ll see a positive difference in your online dating experience in no time. Let me know how it goes!!

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