Ask Ava

Ask Ava: Online Flirting Tips for Men

Woman in Bra on Laptop

Q: Dear Ava. I’ve been told I have a flirtatious personality, and it’s true. I like to flirt with women – all women! I don’t think I cross any lines, even when I flirt with friends or married women, or when I’m in a relationship. It’s about making them laugh and feel good about themselves. One female friend describes it as charming without being threatening. I’ll take that. So I do feel confident in my flirting abilities in “the real world” BUT online is like a whole other universe. It just feels weird without the face-to-face or body language. I don’t get a lot of responses, hardly any actually, and I feel my self-confidence taking a serious nose-dive. How does one flirt online? – Calvin

A: Hi Calvin. Flirting is fun. I like to do it, and I do love men who flirt also. I also completely understand the kind of non-sexual flirting you talk about. If there’s no intention behind your flirting with friends or women in relationships, I don’t see the harm. I have a good friend who flirts like you, and it really is something to watch. Some men have zero flirting ability and it puts them at a tremendous disadvantage when trying to make a connection with a woman.

It sounds like you are new to online dating. Always a bit of a shocker and takes a little getting used to. If you scour through past Cougar World posts you’ll find all sorts of tips for online dating from myself and others, including a few men.

Some online dating sites do offer video chat with other members, which might be preferable for the visual aspect of flirting. Sending a first message is crucial, and you must put effort into it if you expect any chance of a response. The basics of this are: reading a woman’s profile carefully, crafting a well-written note that touches on something about HER, and in your case – not being too flirty out of the gate. Of course, you’ll need a great profile that a woman will be attracted to… not just good pictures! Seeing how flirtation is one of your strengths, you’ll want to meet with women quickly. This is always a good idea because it prevents our expectations growing into fantasies that can’t be lived up to.

Ultimately, don’t worry about flirting online, so much as getting a response from your message… then you meet and work your magic!

Need advice on dating, relationships, or sex? SUBMIT YOUR QUESTION HERE, and who knows, you may appear in the next Cougar World newsletter. -xo Ava

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