Guest Post: Online messaging 101



Today we are getting some fab online dating tips from Cali Bradshaw over at Sex and the Twenties. She is going to breakdown the essentials of a good first message: a crucial component of landing that hottie on your screen. Thanks for the tips Cali!


How to write an online dating message that will get a response.

You spend hours trolling your online dating site without much hope. Person after person, and none of them seem the least bit right for you. Just when you are about to give up hope and accept your fate as a perma-single, you stumble on someone that you might actually be interested in talking to. You check their profile, no fails there, and you decide to send said person a message.

A solid plan, although as most people who have done online dating know, sending a message doesn’t automatically guarantee a response. There are a lot of variables as to why someone may choose not to respond, the most obvious being – your message sucked. To help you avoid this initial rejection, I’ve compiled my tips for writing an online dating message that will actually get a response.

• Read their profile. Well. Like the whole thing. While reading, pick out bits that you find particularly interesting or relevant to you. Maybe even make a few notes. This way you’ll remember what to refer to when writing your message

• Keep your message short – but not too short. If your whole message simply reads, “Hi, you’re gorgeous,” that is obviously bad. But writing an entire novel is awkward too. I’d say make approximately three points in your opening email and keep it to less than 100 words. You are just aiming to pique their interest. You don’t need to sell them on a life with you just yet.

• Talk about them and how their profile relates to you. If they want to know about you, they’ll read your profile, so no need to just regurgitate the information here. Instead, find things you have in common and talk about them. Eg. “I saw you just ran the La Jolla Half. I did Carlsbad once but I heard La Jolla is much harder. Did you have a good time?” If you can’t find a single thing in their profile that you have in common, perhaps you shouldn’t be messaging this person in the first place

• Avoid being overly broad or generic. If you’ve gone out of your way to read this person’s profile, make sure they know it! Saying things like, “it looks like we have lots in common” is useless. For all they know, the thing you have in common could be that you both own a beta fish and that probably isn’t compelling enough to get them to date you.

• Ask questions. When you ask a question or two, the person automatically feels inclined to write you back to answer said question. That being said your question should relate to what the person wrote in their profile, not something random like, “So do you like cheese?”

• Humor, humor, humor. Everyone loves laughing, so if you can fit in something funny, go for it. That being said, don’t force it. If the funny doesn’t come naturally you’ll look like you are trying too hard and you’ll probably turn the other person off.

• Spell check & proof read. We weren’t all English majors, I get it. But a message that is chock full of misspellings and grammar faux pas is distracting. It makes the person on the other end think that you are either not very smart, or you didn’t really care enough to read through your message before sending. If you aren’t good with this stuff, grab a roomie or a friend to glance over your message before you send.

• Avoid being creepy. Chances are you are going to run into people you know (or know of) when you are perusing the online dating sites, however, calling them out on who they are is awkward. On more than one occasion I have had someone guess where I worked or who I am just by reading my profile and checking my pics. Frankly I felt it was a bit weird.

• Set yourself up for success. At the end of the day, a perfectly crafted email doesn’t mean you are going to get a response. I’ve found that in the world of online dating, people seem to think it is fair game to reach out to anyone and everyone – no matter how out of their league that person may be. While I applaud that confidence, I am still not going to write someone back that I am not remotely physically attracted too.

I’m not saying you shouldn’t shoot for the stars. I’m just recommending you be realistic about it. Writing a good online dating message takes time, and that time may be better spent on someone more likely to respond. My rule of thumb is, if you think it is someone you’d feel comfortable approaching in a bar or out in public, then go for it.

These are just a few guidelines to help you in your quest for love online. In the end, there is no “right” way to message someone, but there are definitely some wrong ways. Check out my list of the worst types of online dating emails and avoid writing any of those. If you can do this, you’ll probably be just fine.