For Ladies From a Guy: 10 tips to flirting like a pro online

By Jonathan Roseland

Here are some insights from the fair amount of attention I have received online from delectably clueless aspiring pickup artists of the fairer sex.

For single ladies, social networking apps are one of your best bets for meeting your prince charming; You can see all kinds of pictures, find out about mutual interests, see who your mutual friends are, and even connect intellectually - all before deciding if you want to meet in person. But a lot of you ladies are doing it wrong, if you want to meet a high-quality man and start the relationship off right here are some tips...

Talk like a grown-up.

Good grammar

I'm amazed how many women in their '20s still use annoying teenage MySpace slang. If you want to get treated like a classy lady, talk like one. I recommend the app Grammarly, it's a lot smarter than autocorrect and will make flawless grammar effortless.

Sexy photo etiquette.

sexy photo

I know you love the attention you get from those sexy photos and we men love to ogle, but if you want to get treated like a classy gal, then leave something to the imagination. Just remember that, even on the internet, first impressions are self-fulfilling prophesies of how the relationship is going to go. If I wanted to look at pictures of naked girls, there are a whole lot better options than social media. Keep those pictures of your ass looking phenomenal in a thong in a private collection as opposed to broadcasting them to the entire internet.
Tip: Once you've snagged a decent dude as a boyfriend, send him a sexy pic from your private collection while he is at work before a hot date.

Practice reciprocal photo commenting.

photo commenting

If he leaves you a flirty comment on your photos, return the favor (if you like him). Don't just like it or ignore it, comment on one of his photos.

Practice just a little exclusivity.


If you are dating, sleeping with, or heavily flirting with a guy, don't be doing the same with another guy he obviously knows. Show a little class and please don't put a decent dude in a bro's over ho's dilemma. This is how you get a reputation as a skank.

Don't talk about past relationships.

past relationships

This one should be common sense by now, but it bears repeating. Do not talk about your past relationship failures, at least not from the jump.

Talking dirty.

talking dirty

Oh, please do! You know you want to! However, if you want to set yourself up as anything other than a one-night stand, then leave something to the imagination during your sweaty IM sessions. Also, what's especially hot is if you can mix an intellectual conversation with a little dirty talk. He will remember you as that rare sexy yet intelligent woman.

Do as you say. Say as you do.

do as you say

I think part of the reason for the whole cougar phenomenon is that guys are just so sick of flakey girls. The current generation of women in their early to mid-'20s seem to flake on dates or social engagements they commit to about 50% of the time. Don't make commitments you aren't sure of. Tip: If you aren't 100% sure of a commitment, tell him it's a "maybe" - that you will check your calendar and get back in touch within 24 hours to confirm.

Talking about your kids.

single mom

We live in a brave new era where single guys without kids will date single ladies with kids. However, there are a few rules to this...

  • Bring it up on the first date, and find out if he has kids. Don't be like The Non-Consensual Kicker, a woman I dated who told me that she was childless and then turned out to have two babies - not cool! If he does have kids, then it's acceptable to chat about kids for a little as it's a commonality. If he doesn't have kids, then they shouldn't be discussed unless things get serious. Until such time, your kids shouldn't affect him or your relationship, and bringing them up is a major turnoff.
  • He doesn't want to meet your kids. Not to mention it's wrong for young children to see a revolving door of partners coming in and out of their parents' lives.
  • Drama with your baby's daddy is between you and your baby's daddy - NOT you and the guys you are casually dating.

Do NOT, however, identify yourself as a single mother in your dating profile. Essential reading for single mothers: NEVER SAY THAT YOU HAVE KIDS IN YOUR ONLINE DATING BIO. Pedophiles deliberately target single moms on online dating websites to get access to their kids.
Dose of Truth: The pedophile risk should confirm something that you've probably suspected, which is that you should only be dating single fathers - the men willing to date single mothers, at best, have low standards and won't take the relationship very seriously (I was certainly like this when I dated single mothers) for the simple reason that you're far from being his best reproductive or life partner opportunity. And at worst, single mother daters can be abusive, dangerous predators.

Don't waste people's time.

Waste time

One of the most annoying things is a lady that incessantly flirts online but isn't interested in giving up the digits or meeting in person. This just wastes everyone's time. I've unfriended more than a few of these. Don't flirt with a guy you wouldn't give your phone number to. Don't give your phone number to a guy you wouldn't meet in the real world. In fact, if you really aren't interested in a guy, unfriend him, he will (or should) appreciate it.

Do a hybrid (group/one-on-one) first date.


For your first date, invite your prospective prince charming to show a little social initiative and arrange a group outing. If you met on social media, chances are that you have mutual friends. If a guy doesn't have enough social influence to pull together a group of friends, he's probably not worth dating. Do arrange for some alone time before or after the group outing to get to know each other one on one.

For your reading pleasure, single ladies, I recommend checking out The “Bad Boy” Syndrome, by my delightfully witty and insightful wife - give ear to her advice and you'll enjoy, I dare say, a douchebag-free existence.


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