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5 Common Online Dating Introductions Gone Wrong, and How to Do It Right

Because a winky face probably won't make the right first impression.


Art Credit: Shannon Lee Miller

Online dating has never been free from awkward moments. But some are more damning than others, usually the ones that involve bad first impressions. For instance, nothing makes a girl want to crawl away from her computer and wait out another 6 months of singleness like a solitary winky face received from a hopeful suitor online.

But rather than wading through a pool of un-inspiring introductions, why not send a few super smooth introductions yourself? Sarah Gooding, a dating coach from Plenty of Fish, shares 5 common online introductions gone wrong and how to do it right.

01. Avoid giving too much information.

Intro Fail:

Hi there,
Your profile caught my eye.
I’m a 33 year old single female living in Portland. I’m divorced with 2 beautiful children.
By day I’m a Freelance Writer, and I dabble in Carpentry, Lighting, Audio, Video, and just random stuff. I'm a bit of a workaholic! Should we happen to go for coffee some time, I'll tell you all about it! In my free time I enjoy camping, Netflix, skiing, beer, yoga, laughing, avocadoes, swimming, travelling, knitting and shopping. Right now I’m re-watching Beverly Hills 90210 on Netflix. LOL. Hope to hear from you soon.

Why this message doesn’t work?

There is plenty of time for him to learn that you don’t get along with your parents, you own 6 cats, and are up to your ears in student debt. But a first message is not the place. This message reveals too much information and is much too long.

A great first message should provide new information that can’t be found in your profile, should be positive, and should reflect the best you. But remember, keep it to 3 or 4 lines, The more you write, the more daunting your message will be to read and the less likely he’ll be to reply.

02. Easy on the emoticons

Intro fail:

You're so cute!!!!!
Just had to say hi!!!
I'm Kelsey:):)

Why this message doesn’t work?

I have yet to meet a man who considers being called “cute” a compliment. Using words like cute, adorable, stunning, dreamy, delicious, and so on, will never be considered complementary in the eyes of a man. If you want to compliment a man, keep it to a minimum and pick attributes that men value like ambitious, accomplished, or active.

As for the punctuation embellishments, it’s important to use them sparingly—if at all. While a smiley face or exclamation mark can add some extra emotion or personality to a message, too many exclamations marks can sometimes be associated with a lack of maturity or intelligence.

3. End your message with a question.

Intro fail:

Hey there:)

Why this message doesn’t work?

This lame attempt at a message may get the attention of a few, but it likely won’t get the attention of the men you are really interested in. If you are going to be proactive and send a message to a guy you’re interested in, put some extra effort into it to ensure you get a reply.

Read his profile and then ask him about something from his profile within your message. This will dramatically increase your chances of a reply. Some easy ways to do this are to ask him about one of the interests that he’s listed or ask about one of his photos. Where was that photo taken?What’s your favorite mountain? If you can’t think of any questions, why do you want to message him in the first place?

4. Try a gentle nudge.

Intro fail:

You sound like you've got some good things going on. Nice that you're active and you place a great deal of importance on fitness. Want to grab a glass of wine sometime this week? Call me at 646-874-98** or email me at jsm*****

Why this message doesn’t work?

Although it is perfectly fine to take charge of a situation and ask a guy out, a first message is much too soon to be giving out your contact information. Giving a man your contact information in an introductory message gives off an air of desperation because you have yet to know who this person really is.

A gentle nudge, after you have exchanged a few messaged back and forth, is always better than a direct offer that requires an answer. For example, rather than writing “Want to grab a glass of wine this week?” Try saying, “I’m always up for grabbing a glass of wine if you’re ever in the area.” If he doesn’t take the opportunity to then ask you out and make solid plans to meet for a date, he may not be interested. Next!

5. Be positive.

Intro fail:

Your profile caught my attention. Are you having any luck on here? I’m not. So many creeps. Chat soon. Jenn

Why this message doesn’t work?

An introductory message is not the place to discuss your online-dating experience. Although you may feel that this is a way to relate to someone you’re interested in, it can easily take the conversation toward the friend zone and doesn’t make the guy you’re chatting with feel very special. Everything you write in a first, second, or third message should be upbeat and positive. Any indication of a complaint or negativity will turn a good guy right off. Remember that positivity increases attractiveness and negativity does the opposite.