10 Do’s (And 10 Don’ts) Of Wooing Women Via Internet Dating Sites

Jack Frog / (Shutterstock.com)
Jack Frog / (Shutterstock.com)

In our experience, guys on Internet dating sites are completely clueless as to how to get a quality woman’s attention. So we’ve compiled a list of do’s and don’ts for men looking to date a half-decent female. If you’re just looking for someone completely desperate, a woman with really low self-esteem, or an STD, by all means ignore our advice.

When messaging a woman for the first time…


1. Reference something you actually read in her profile.
2. Compliment her without sounding like a pervert.
3. Use punctuation, proper grammar, and spelling. Otherwise, you just come off like an uneducated douche.
4. Ask a question to show you’re interested.
5. Make sure you know which one she is if she posted group shots.
6. Allow time for her to respond. And, if she doesn’t, let it go!
7. Mention something you have in common.
8. Take a hint (especially if it’s not at all subtle).
9. Let her choose or approve the location if you choose to meet so she feels comfortable.


1. Address her as though she were an ice-cream sundae. In other words, no “mmmmm…,” “yum,” or anything of the sort.
2. Post pictures of you hugged up with another girl unless you specifically mention that she’s your sister.
3. Be too aggressive…it sends a rapey vibe and will scare them away.
4. Ask for, or even reference, sexual favors.
5. Ask her if she’ll be your sugar mama and/or roommate.
6. Mention your ex.
7. Brag about yourself. Let her find out for herself how great you are.
8. Ask her bra size, how big her nipples are, measurements, or any other specifics about her body. It’s none of your damn business.
9. Ask if she’s bisexual or into threesomes. If she is, she’ll offer that information when the time is right.
10. Last, but certainly not least…for the love of God, do NOT send her a picture of your penis! Not even via text or email. Not even just the tip. And if she asks for one, run (unless you’re one of those guys just looking for an STD).

On behalf of Internet daters everywhere, we thank you. Thought Catalog Logo Mark

Retrieving our sanity, one word at a time. Passionate about animals, education, and craft beer.

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