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Top mistakes men make when sending that first email

You only have one chance to make a good impression. Nowhere is that more important than in the online dating environment. Miss the chance and you’ll never recover. There’s no going back and over the cliff you’ll go. So here’s some tough love regarding some of the best ways not to make a good impression. Or, to put it another way, how not to come off like an asshole.

Unwelcome sexual advances or comments.

Stay away from the flirty or bawdy comments until you are sure you can make them. It almost certainly isn’t in the first email.

Talking about yourself.

Spend too much time talking about yourself and you’ve done the worst job ever about that first impression business. Telling her how cool and suave you is just a waste of both your times.

Not asking questions.

This goes with the above. Find something, anything meaningful to ask her about and if you can’t do it, go home because you’re wasting your time trying to find a date. Oh, sorry, you are home.

Ignoring what’s in the woman’s profile or failure to comment on the woman’s profile.

If you can’t find something to comment on in her specific profile, you might as well be sending a form letter, and believe me, it will show.

Too much emphasis on the physical.

It’s OK to say how attractive you think she is, but don’t dwell on it too much. Do too much and you’ll come off creepy. See below.

Asking for a phone number.

It’s too early for this. Don’t do it. Creepy.

Mentioning how rich you are.

If you spend time telling her how rich you are, or even suggesting it in an effort to “big time” her, all you’ll do is turn off 99% of the ones you want to impress and attract the 1% you don’t. This is a scientific fact and the percentages have been independently verified by history.

Goofy, corny humor.

Humor is funny when two people “get” each other. If they don’t, the humor doesn’t work and instead of being a glue to hold your relationship together, it’ll dissolve it faster than turpentine. Be careful with that peculiar and quirky humor of yours.

Crazy, ass-clownish compliments, like: “You’d be perfect if you lost 15 pounds.”

Nuf’ said.

Sending your phone number in the first email.

If you say in your email: “Here’s my phone number, call me.” It really says, “Here’s my number, 1-800 277-25696 (1-800 ASS-CLOWN) Hit me up!” That’s what it really sounds like when read out loud.

Using bad grammar, or misspelling words:

Expressions such as, “I realy like you’re hare!”, or; “Your beautifull!” will kill your chances before you get started. Use a spell checker if you have an doubts about your ability to spell big words. If you can’t spell well and can’t manage a simple sentence without grammatical errors you’re [sic] chances are simply not good. Using a bunch of texting abbreviations won’t help you either. All you’ll do is come off as dim, silly or lasy [sic].

Creepy talk.

We’re not talking about your odd love of small animals here. It’s hard to believe but expressions such as “I like kissing”, or “I like apples with peanut butter” can be risky in the first email. Even something as seemingly innocuous as “I like pie”, taken out of context or misinterpreted, can be a real turn off. If you think what you might be saying can be taken as creepy, it probably is. Avoid odd, strange, unconnected expressions at all costs.

Self deprecation or sycophantic speech .

Saying things such as “I’m probably too old/young for you.”, “I’ll do anything to meet you! Anything!” will kill you, too. Come off too weak in your first email and you’ll never recover from it. Never.

Telling her you don’t have a photo – yet.

If you have say something like, “I don’t have a photo up on the site yet,” you might as well have said, “I’m an ass-clown with something to hide but I’ll send you a secret, creepy photo if you beg me for it.”  Go home.

Think About This!

Having great online dating photos is the most important thing you can do when dating online, so visit LookBetterOnline and and see how with great profile pictures we can help make your online dating experience successful and more fun than you thought possible!








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Comments (3)

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    All of those are so true!!

    And yes, if you don’t have a photo you are doomed from the start.

    No photo = married.

    At least, that’s what we girls will assume.


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    Great article Dave
    I like your writing style…Keep them coming!


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    Ha Ha, Dave, all of the above are absolutely bang-on. I used a dating site a few years ago to meet my current partner, and gained quite a few highly-attractive female friends on the way.
    I was fascinated by the inept nature of the first mails the women told me that many men send: blatant sexual innuendo, showing off, egregious spelling and grammar; or simply having nothing interesting to say, and showing no real interest in the woman’s life, interests or personality.
    They nearly all read as ‘I’m desperate for a shag, with anybody, so call me now! Most women might agree that this approach is not likely to work 🙂
    Photos are so important too, so good luck with your business. Like you, I’m amazed at the rubbish images some people use.
    Dating sites are a fantastic innovation – I’ve met some stunningly intelligent and beautiful ladies through them (I live in Asia), and made lifelong friendships.
    Good luck everybody!


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