Eek!! That Awkward First Message…


Our members dread sending that first message so we’ve created a quick guide for helping you maneuver around the awkward initial approach.  As with your “About Me” section, keep it casual and friendly!  Clever introduction, make a compliment, ask a question.  Bam!

Here are some “Do’s”

  • Keep It Short: If you are writing more than 5 sentences, you’re either writing too much about yourself or writing too much about them.  You don’t need to cover everything in the first message – that’s what a date is for!
  • Stay Positive: A lively message conveys confidence and positive energy.  We know it sounds hokey, but try smiling as you type – successful salespeople smile when writing and so should you!
  • Compliment: A little flattery goes a long way, especially when conveyed with some charm or humor.  For example, “woah – is that a fresh designer dress in every photo? – did you buy out Carrie Bradshaw’s closet?” or “really cool how you play in a kickball league – but what’s the real ratio of kickball to booze hehe?” or “wow! really impressed by your profile! You put mine to shame!”
    • While it’s OK to compliment someone on physical appearance, be tasteful!  Instead of “you have a gorgeous body”, try “you look beautiful in your photos, especially the one with…”
    • Be honest. If you’re making up a compliment just to score points, you probably won’t come off as genuine.
  • Ask Something: We can’t stress this enough: most people would like to talk about themselves and their experiences rather than listen to you.  Use the information provided in their profile to dig deeper.  But be careful, some folks are weary getting personal questions on the first interaction, so ask about one of their interests or a place they like in the city.
  • Women: It’s 2020: don’t be shy.  Go ahead and send a message or a smile.  That perfect guy might be a bit shy or think you’re out of his league.  All he needs is a little nudge.  You’re also doing them a favor, because if you initiate the conversation, they can speak to you for free!  What better way to start a relationship than with a gift!? :)
  • Men: If you don’t hear back, you may want to try again.  A woman may find your persistence endearing… BUT don’t go beyond two messages… at that point it’s just nagging.  And don’t focus on your initial failed attempt.  Instead, stay positive and focus on the bright future.
  • Proofread: PLEASE re-read what you wrote before sending the message.  Your phone rang, you answered a text, you yelled at your friend – distractions will jumble your message without you noticing.

Here are some “Don’ts”

  • Don’t Be Desperate: Unavailable is sexy.  If you’re free to meet up Mon-Sun anytime after 5PM, you likely have a boring life.
  • No Disclaimers: You don’t need to apologize for using online dating as a medium for conversation, nor do you need to reaffirm that you’re not one of those “other” creeps that use online dating.  The fact that you’re a member of Loveawake already makes you exceptional – and raising these topics just associates you with those negative concerns.
  • No Last-Minute Booty Calls: Sending a first message on Friday at 7PM asking to meet up that evening makes you look desperate or makes the other person feel like a “back-up plan”.
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Alex Wise served over 5 years as relationship expert helping women from around the world figure out the men in their love lives from an honest, male perspective. Alex is one of the contributors and editors for dating website. He is passionate about thought leadership writing, and regularly contributes to various career, social media, public relations, branding, and online dating communities.