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Breaking the Ice Online: The Good, Bad and Ugly of First Messages


When it comes to online dating, taking the initiative to break the ice and send that first message is often the hardest part. After all, there’s something inherently awkward about reaching out to someone over the internet that you’ve never spoken to before in hopes that they may think you’re cute and interesting. What if they think my message is lame? What if they don’t write back? What if they reject me?! It’s natural to have these kinds of thoughts. However, crafting a quality ice breaker isn’t as daunting as you may think. However, with that said, many people still struggle with writing a suitable first message.

To give you an example of what you should and shouldn’t do when it comes to sending that first message, here’s a few real life examples of online icebreakers that range from good to downright terrible.

The Good –

  1. Short and sweet 

“Hi there. Nice to meet you! I see that you’re also really obsessed with sushi. What’s your favourite sushi spot in the city?”

What’s great about this message: It’s short, sweet and shows that you’ve read the other person’s profile. Online dating has the tendency to feel slightly anonymous and impersonal – like everyone you meet is just playing a numbers game, sending out as many generic messages as possible just to see what they come back with. By referencing something in their profile, it shows that you took the time to learn a bit about them and see them as an actual person with interests (I know, revolutionary right?!)

Also, keep in mind that a great message doesn’t have to be a novel. In fact, keeping things brief and concise is ideal. This message is easy to digest and provides a great jumping off point for an actual conversation.

  1. Variation on a theme

That’s very brave of you to admit you’ve never been camping 😉 Some people can give you a really funny look when you tell them that. I love hiking and being outdoors however I too have never been camping. I think I would be pumped about trying it out with the right person but I have to admit the idea of not having easy access to a shower puts me off a bit!

If you like Thai food have you tried “The Little Thai Place” on Ventura? I go there often with a few friends of mine and we all agree it has the best Pad Thai in town right now.

What’s great about this message:  This is a good example of a longer message that still manages to be focused and personal. It comments on the other person’s profile and finishes with a question. If you’re not sure exactly how to break the ice, asking a thoughtful question about the other person’s interests is always a good place to start. Not only is it a legitimate way to show your interest in the other person, it gives you something to talk about.

The Bad –

  1. The one word message


What’s wrong this message: It’s only one word! When I receive messages like this I’m tempted to respond with Lionel Richie lyrics (“is it me you’re looking for?”) Although Jerry Maguire is able to get women to fall in love with him at “hello” you are not Jerry Maguire. Not only does a one word message come off as incredibly generic and lazy, it also doesn’t give the other person much to go on when it comes to continuing the conversation. Same goes with messages that just say “Hey” “Hey Sexy” or “What’s Up”

If you’re legitimately interested in the person, you need to write a couple of coherent sentences.

  1. The never ending story

(February 1st)

“My name is Bobby. I am new to the area… came about 4 months ago. As summer comes closer, I feel myself itching to get out and get active. Do you play volleyball? Rollerblade? Dance salsa?”

(February 6th)

“How would you feel about meeting up for a walk along the water followed by some drinks or food? It would be great to get to know you.”

(February 15th)

“We could also spend some time getting to know one another over this site, before meeting up… is that something you would prefer?”

(February 20th)

“Hi 🙂 Was your Saturday as sun-filled as mine?”

(February 25th)

“Sooo, after visiting my profile, do you think that I have something to offer that you might be interested in exploring?”

(March 1st)

“Hi …. how do you feel about bdsm? I would be curious to try out one such relationship… being dominated by a woman sexually… would you be interested?”

What’s wrong this message: Although it seems that “Bobby” started off with good intentions, when I failed to write back, he continued to send messages…and more messages, ending with one that was overtly sexual. If someone doesn’t write back – don’t sweat it. Maybe they’re not very active online and they might write back at a later point in time – or maybe they’re just trying to quietly let you down. Either way, continuing to contact them after they haven’t responded is a surefire way to kill your chances (and likely creep them out in the process.) Unless you’re on an adult dating site, sexual messages should be avoided at all costs. In the case of “Bobby”, the ice has been shattered to the point where it’s now a certified danger zone.

The Ugly –

“Hey Mamacita u lookin’ sexy? u lyk spanking? Imma git @ u l8r babe. rite? Yeh! imma imma get them landz”

What’s wrong this message: EVERYTHING. Overtly sexual? Check. Grammatically questionable? Check. Equal parts generic and completely nonsensical? Check. Impossible to respond to? Check. If your ice-breaker messages look like this, do not pass GO. Instead, return to the top of this blog post and master the art of sending concise, thoughtful messages. Trust me, you’ll thank me later when the object of your affection doesn’t respond with Lionel Richie lyrics.


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