Online Dating: When to Respond to a Wink or Email

When to respond to a wink or email in online dating. If your profile is on an online dating site there will be times when you get winks or emails from people who don’t seem the least compatible. Why did they choose you and where did they come from?   Haven’t you wondered why the guy in Portland, Oregon thinks he could successfully date a woman in Florida?

In my last post I talked about online dating photos and how to use them to your best advantage. Today I want to talk about responding to guys who wink or send emails.

I recently got some winks from a bevy of men all at the same time. Odd, very odd, and less than 24  hours later three of them have pulled their profiles. I think I’m being pranked. But how would I know?

  1. If you’ve been winked at, which even nonpaying members can often do, has this person looked at your profile? If the answer is no, you might stop to think about the fact that his interest is driven by the first few visible lines and/or your picture. That could mean he’s rushing in without much thought. Or that you’ve done a great job with your opening lines and photo!
  2. Does he live nearby or have a distance range that includes your location? If the profile states an interest in women within 20 miles and you live 200 miles away then he’s probably just bored and winking at everyone.
  3. What can you tell about him from the profile? Does he seem like a good fit? Are his interests in line with what you’re looking for?

Most of the time women are eager to respond to men who wink at them. It is an indication of some level of interest and you will want to consider it. So what do you do?

It is good manners to respond in some fashion. lets you send an automatic ‘no thanks’ reply. You can always write a no thank you letter yourself with a little more detail if so inclined. Either way, the intent is the same. If you’re interested in him you can wink back. You’ve upped the ante and it’s his move. If you’re really interested you should write an email and tell him. This guy might have winked at several women so you should move quickly if you want to play. It’s a competitive market.

However you decide to respond, take the time to check out all the details of his profile first. Don’t send an encouraging letter if he’s a smoker or has dogs and you hate both. He’s not going to change habits and you’re not going to be able to ignore those things. It’s tempting to engage, after all, that’s what online dating is all about.  But, you have to be realistic.

Suppose he’s a motorcycle rider (and for some odd reason many middle-aged men have bikes and show them on their profiles) and you aren’t, but you like his looks. Send an email telling him you’re interested, that he find him attractive and you’d like to get to know him. And, somewhere in there, tell him you’ll never get on his bike but if he still wants to correspond you’d like that. Tell the truth.

You should already know what your ‘deal breakers’ are and stick to them. Ultraconservative is one of mine. And, no matter how cute, how appealing his book list or interests, I know we won’t be a match. So, I let him know that. And, I move on to a more realistic match.

It’s easy to get caught up in the game, like being in an ice cream shop and wanting to sample every flavor. There will be times when you’re not getting much activity and any wink or email is exciting. The key is to be objective about the guy before diving in. How you decide to respond will depend on your ultimate goal.  If he’s really not your type don’t waste your time. Send him off nicely and keep looking.

Next time let’s talk about how to carry on a conversation with two or more men at the same time.


Online Dating: When to Respond to a Wink or Email — 8 Comments

  1. “If you’re really interested you should write an email and tell him. This guy might have winked at several women so you should move quickly if you want to play. It’s a competitive market.”

    There’s something about this paragraph that send shivers down my spine. I’d prefer to be alone than to start competing for love or attention; guess I don’t have the personality for it 😉

    • I understand. It is one of the drawbacks of this type of dating. I did a little research on my community and in the age range of 50-65 there were close to 600 men and the same for women using There are advantages to online dating and disadvantages – the candy shop mentality is problematic for some. And, there are others who love it!

  2. I was online right at the start of the wink. I never know what do do about those so I just ignored them. I’m still not clear on why people do this. If someone looks interesting, why not just write to them? Are people being lazy when they do that? Is it a real expression of interest?

    • I’ve always wondered. My thought is that some times they aren’t paying members and are using that to gauge whether you’re interested and will email. Of course if you’re not paying and get an email you don’t know who it’s from til you pay! And, that’s a trap sometimes.
      And, other times I think it’s just… mischievous? I really don’t have a clue.

  3. I’m a man who sends a wink if I see a woman I find interesting. I do it because it is a way of discovering if she is interested without me investing too much of myself in the contact. In other words, I won’t be devastated if she does not answer my wink. There must be many others, both male and female, who likewise feel the need for the ‘wink’ or the dating sites would not make it available.

    • Hi Murali,
      I send winks too and I respond to them when they’re legitimate-though figuring that out can be challenging. And, I agree with you that it’s an easy way to indicate interest in a noncommittal way.

  4. I’m in the over 55 age bracket, and quite often get a lot of winks from younger ladies. Before I respond, I check to see if there has been any prior interest. If not I see amessage saying thankyou. Your expression is appreciated, If there was prior mutual interest, then she will receive a message asking her to contact me again. I realise there are some younger ladies who feel intimidated contacting older men, or feel they should be pursued and not the chaser. Myself, I express my interest in a lady by message, as I feel flattered when I receive a wink, but it can be a passing boredom. Written messages give you time to consider whether the recipient is appealling, or just a flighty fancy of thought.

    • Bob,
      Thanks for commenting. It is useful to have a framework on how you respond. Like you I have experienced random winks that really meant nothing.

Leave a Reply