Online Dating is an easy way to meet singles, but with the growing # of people online, it’s very easy to get lost in all the profiles, messages, and “winks”.  I’ve posted two blogs about what Not to do in your profiles, but want to really focus on using the Messaging feature of online dating.  The first message is extremely important.  Here’s a way to guarantee that you don’t lose her interest before she has a chance to check you out.

Follow this checklist & you’ll increase your chances of being noticed:

1.  Make an Observation

If you want to get a reply from this woman, make sure you actually took the time to learn about her by reading her profile.  Select one interesting topic that she talked about and focus in on that.

2.  Share something about Yourself

Sticking to the same topic, share something about yourself.  It could be a joke, a story, or just that you love it too.  Something a little more in depth and a few words showing your personality is ideal.

3.  Lead to a Date

I said Lead, not ask for a date immediately.  Asking a girl out in the first message is creepy, but showing that you’re interested in taking the conversation there is intriguing and shows us that you’re not going to chit-chat with us for a month before actually asking us out.  Having a man display assertiveness and confidence in the first interaction is…well, hot.  Nothing is sexier than a man who knows what he wants and who’s a gentleman in his approach.

Below are examples of messages I’ve received.  The ones in GREEN are great – they cover all of the Must’s that your first messages should include.

These men showed that they’ve read my profile, their own personality comes through, and are being assertive while leading the conversation to an actual meeting.


Hi M,

Totally not making any assumptions here… IF you decided that you wanted to meet me for happy hour sometime, and we got along well and decided to continue to hang out, I would gladly taste-test any fancy meal that you would like to cook.

I think it’d be fun if we did a cooking class together sometime. What do you think?

Hope to hear from you.


Hey there,
I came across your profile and think you’re awesome. And pretty dang cute. You seem really active and outgoing.  I, too, enjoy a nice glass of wine and would love to have a debate about our favorite documentaries. It would be awesome to get to know more about you… so feel free to write me back if you’d be interested in knowing more about a guy who will run around the town with you. 
– Scott
And here are some that aren’t great.
(Big bonus point though for actually sending the Message, vs just Winking)
These guys also didn’t show that they read my profile, found anything interesting about me, and they’re not leading the conversation anywhere.
Morning Cutie!
How are you? You sound like a cool girl. I’m also looking for a partner to share this with. I’d love to meet someone who is intelligent and can have fun doing anything with, be it going out for a nice dinner or camping or anything in between. What do you do for fun?
This is just him rambling on and on about himself, and using generic phrases describing what he’s looking for. Also says that he didn’t read my profile since he’s still unsure about what I do for fun.



Hey I read your profile and you seem pretty interesting. Let me know if you want to grab a drink sometime.

He’s saying you read my profile but this email is too generic & not assertive enough.  There’s no question here either, so it’s not making me want to keep this conversation going.
There’s also the type who are too forward and come off too aggressive/assertive.


Wondering if you’d be open to meeting at Starbucks briefly to chat sometime?
He’s asking for a date too fast and not sharing anything about himself.  Women still need a little conversation before we’d be open to meeting you.

Hello, Every once in awhile you see someone, and without knowing anything else about them you know that you would enjoy their company. It has to do with facial characteristics and body posture. Anyway, I don’t know much about you, but I know that you would be fun to spend time with and to get to know better

This one is kind of cute, but is a bit too much.  This guy sounds like he’s trying too hard to be Mr. Romantic and make it feel like it’s meant to be.  Even if his profile is great, I’d be hesitant to talk to him.
Please remember to keep it short, follow the 3 key points in your message interactions, lead to a meeting, flirt, and be careful to not waste too much time going back & forth.
Hope these examples are helpful!