Internet dating—to flirt or not to flirt? Must-know secrets for success

I’ve participated in your classes in the past.  I just started online dating a few days ago and I feel like my head is going to blow up! I am completely overwhelmed and not sure how to navigate the whole thing.

People are mostly sending flirts, and I am not even sure how to respond to this. Frankly, I wish that they would just e-mail me. I am not sure if I should send flirts to people who interest me or maybe just e-mail them or wait for them to make the first move. I haven’t a clue. One guy sent me flirts, and then in the first e-mail he sent me he asked for my number. I didn’t give it to him because I don’t know if it’s too soon or what. HELP!

Thanks, Brittany


I’m so glad you asked this question. There’s so much I’d like to share with you, but it simply would take too long to write it, which is why I’m now putting together an Internet Dating Workshop. I’ll tell you more about it once I have solidified the date and time.

For now I will address the “flirt” issue and direct my advice to both men and women on this point.

Men—Sending flirts is like saying, “Hello” It’s polite and increases the woman’s awareness of you but does little more than that. Women don’t often know how to respond, and so contacting you back makes them feel insecure and uncomfortable. Furthermore, flirts often leave you looking less confident. From your perspective, that may not make sense because sending a flirt seems like you are putting yourself out there, but from a woman’s perspective it feels like the bare minimum when it comes to investment and effort. Like texting, it seems easy and even lazy, and it fails to make her feel like you’re personally investing in her. Additionally, it feels like you’re leaving it all up to her to make a lasting connection. Starting a conversation is hard for her too, which is why a man who makes a good attempt at starting a conversation seems more confident and interesting. Remember, “It’s Not you—It’s Your Technique.” So instead of sending flirts, use this technique instead:

Send her a message stating, “Hey, I checked out your profile. You seem like a fun person (or it seems we might have a few things in common). Please check out my profile, and, if you like what you see, write me back.” You could then follow this up with a personal comment, compliment, question, or request that shows you’ve actually invested enough to view her profile.  For example, you could add, “Oh, and by the way—you have a great smile,” or “You said you just came back from New York. I would love to hear about the places you visited while you were there.”

Making a comment about something you read on her profile or giving a personal (nonsexual, which includes never using the word “hot”) compliment is a great way to increase the possibility of her responding back.

Women—When it comes to initiating flirts and messages, you need to know that doing this has a very low return on investment. If you simply must make sure he sees your profile, then go for it, but I’ve found that you’ll get less than a 10% response. I recommend instead that if you aren’t getting attention you ask for others’ opinions about your photo and that every few weeks you throw in a new photo to see if you get more responses. Your photo is everything online. Make sure it represents your best angle, reduces glare or any shininess on your face, and creates a feelings of softness and warmth. Don’t go all out and get glamor shots, which may make you look unnatural. Instead, get a photographer or good friend to help you take a bunch of pictures in good lighting. You might even find some recent snapshots that you feel make you look naturally beautiful and fun. Chose a recent picture that you feel creates a positive, happy, or fun view of you, rather making you look serious, sad, or pensive. When it comes to your profile, don’t tell people what you don’t want. Tell them what you like to do, places you like to go, things you have done recently, activities you enjoy, etc. This increases a man’s likelihood of coming up with questions or comments that can get a conversation going. You can even mention some things you’d love to tell him if he asks. For instance, “I recently came back from a fun vacation. I’d love to tell you about it, and I’d love to hear about the places you like to go on vacations.”

When responding to flirts, don’t just send a flirt back but give an actual response. Simply say, “Thanks for the flirt. I noticed that you enjoy hiking (or something else from his profile). I’d love to learn about your other interests as well.” Then wait to see if he responds. If he sends another flirt in response or fails to respond, don’t waste any more time on him.

When it comes to giving out your number, most men won’t ask for your number until you’ve sent at least three e-mails back and forth. However, men will stop writing between the third and fifth e-mail, especially if you’re both having a hard time keeping the conversation going. It really is in your best interest that you move from e-mailing to calling. There really is no harm in this if your phone number is unlisted. To find out for sure, type your phone number into the Google bar or go to If you type your full number in and Google responds with your name and address, your phone number is not safe to use. Contact your phone company and ask them to mark it as unlisted. Once you can no longer see your name and address on a Google search, you’re probably safe in giving out your number. You may feel you want more of a connection before you do this, but you’ll be amazed at how much more you can discern about someone over the phone than through e-mail and how much time you really may be wasting by only communicating by e-mail. Additionally, both of you are looking for a connection, and if you don’t start to talk by phone within a few weeks, one or both of you will loose interest in the other.

I hope this helps. Good luck,



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5 thoughts on “Internet dating—to flirt or not to flirt? Must-know secrets for success

  • Alisa,

    Thanks for the GREAT advice! I’ve hated internet dating in the past, but with your advice…I just might try it again! I believe VERY strongly that it is the man’s role to pursue–your advice allows that to happen! Thanks again!

  • Alisa,

    Thanks for your post I too have tried Internet Dating and after sending out over 50 emails similar to yours, I had a grand total of 4 people who responded, I thought that it was my profile or my picture, which caused such a low return. Talking to other guys though this seems to be about the right response rate, so in my experience it is not much better for guys. Also how do you feel about the chat feature that many of the services have now do they help or are they just a big time waster?

    • Live chatting can be a good idea; however, keep a close eye out of the possibility that some of the people you are chatting with could be in a pretty bad place in their lives. This is particularly the case if you are chatting after 1 a.m. For example, those who chat late at night often have drug and alcohol addictions that keep them up late, they don’t have jobs, or they have a compulsive need for attention or sex. If you use good boundaries about how long you chat (20 minutes versus 2 hours), when (at 10:30 p.m. instead of 2 a.m.), and what you will chat about (experiences and things you enjoy versus sexual explicit conversations), you will most likely find people who are in a good place in their lives too. After chatting for a while don’t be afraid to say: women – “I’d love to have you call me” (then wait for him to ask for your number, which you should give by message not chat); men – “It can be hard to get to know someone by email and chatting. Would you feel comfortable letting me call you?”
      I hope this helps, Alisa

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