How to Respond to an Offensive Online Dating Message

Posted by in online dating after 40, single women over 40 | 5 comments

How do you respond to that seemingly offensive online dating message? This case study illustrates how one clever message could turn things around.

As a dating coach for women over 40, I find many women at this age are jaded and tired of dating online. As a result, they often write men off for what may seem like an offensive online dating message at first glance. In today’s post, I want to give you another perspective as to why men sometimes write messages that feel offensive. I’ll give you some ideas as to how to respond to those seemingly offensive online dating messages without being nasty. 

How to Respond to an Offensive Online Dating Message

I’d like to share one of my own personal online dating stories. In a recent search on OkCupid, I came across a profile that stood out. Pictures: good looking guy with funny captions. Check! Profile: witty without being obnoxious or sarcastic. Check! His values seemed aligned with mine, and I was intrigued, so I wrote the first message—-which I highly recommend women do if they want to find love online.

Here’s how it went down…

online dating message

NOTE: I rarely find a man’s profile to be as funny and endearing as his was. That’s why I chose to open by mentioning how his humor not only resonated, but that I liked he also didn’t use the standard overused line, “My friends think I’m hysterical.” Or worse, “I’m really funny. I’ll keep you laughing, and I hope you don’t have a bladder problem.” (True story. I saw that in a profile once.)

His response:

online dating messages

Really? This offended me for a number of reasons. One, he didn’t thank me for my kind words. What happened to social graces? Two, after answering my question about Father’s Day, he mentioned something he had read in my profile about only dating Jewish men.

While I appreciate when a man takes the time to read my profile, did he think that bashing Jewish men in politics would be endearing to me? I grew up Orthodox, and because of my traditional upbringing, I find that I’m more comfortable with men who understand and respect my heritage.

What he did in his initial online dating message was find fault in Jewish men in the political arena. Calling these men boys who never grew up came across as bitter to me. Whether I agree with his assessment or not, I don’t advise engaging in a negative/bitter discussion about ANYTHING in messaging, especially if you’ve never even met!

I ignored that message. I really had nothing to say.

And then he wrote again…

online dating messages


WTF? At this point, many women would have ignored, blocked, or reported this guy to the OkCupid police. First he bashes Jewish men in politics, next he gets sexual. Not so charming, right? This guy must be a jerk….

I cropped it to protect his identity, but he signed with his full name, which I interpreted as an act of trust, of showing your full cards so to speak. So, I chose to have fun with my response. Why not? I was curious as to what he’d say, and there was only one way to find out. online dating messages

That last line about the bouncy castle was my attempt at keeping it light, not harsh or reprimanding.

I was prepared for any response. He could have ignored me. Or he could have been angry or obnoxious, like another guy on Tinder who went from being a gentleman to saying “F#@*k off” because of a question I asked!

His response surprised…and delighted me!

online dating messages


And this is why you don’t write men off so quickly. See how he rose up to his higher self instead of stooping even lower? It could have gone either way.

My favorite part? “I promise I will bring the ‘smart, classy, and funny.'” As a woman of value, when you respond to seemingly offensive messaging without being defensive or shutting a man down, you are opening yourself to receiving the best possible answer. How he responds to you taking the high road will show you his character.

I wrote back:

online dating messages

Notice that I began with humor and appreciation, and I didn’t just agree to drive 45-minutes to meet him without speaking first. That’s an important standard for me, so I shared my number and gave him a window into my availability.

His response:

online dating messages


And there you have it.

What began as a message that offended me, turned into a warm and fun connection. We haven’t yet spoken, so I don’t know if there will be a first date, but that’s not important to the message I want you to take away: DON’T WRITE PEOPLE OFF BEFORE GETTING TO KNOW THEM A LITTLE BETTER.

Online dating can be awkward and impersonal. The purpose of online dating is to meet and see if you click in any way. Yet, many people never even get to that first date, because they either write people off too soon, or they don’t initiate contact in the first place.

Get curious, be open, and don’t take that online dating message so seriously.

What’s your takeaway from my messaging story? I’d love to hear your thoughts!

P.S. Want to stand out from the crowd and find true love online? Click here to learn more about my highly successful online dating course.




  1. I find it difficult to navigate online dating. There are so many scammers and losers… not much to choose from really. Most people online are not honest; they live in their own little “virtual reality”. I’ve gotten to the point I really don’t trust any of them to give them much of a chance at all. i am 61 almost 62 and the age range I like to consider is from 50-64. What I find is a whole lot of inflexible, boring, “I love to drink beer” old farts with a ton of hair on their faces (because none grows on their head…I’m not opposed to bald…but an overgrown face cactus doesn’t make up for hair on the head!) as though razors have left the planet. Who wants that? Then, there are the “pretty boys” with vibrant profiles (20-30 foreign somethings that have borrowed “in English) profiles from a hundred other sites) scammers looking for a vibrant middle age woman (to relieve her of her sanity and belongings while she keeps them in the manner to which they could become accustomed). Whatever happened to real, available nice gentlemen who also have a life and something going for them??? Sure there are always profiles to look at online… but that doesn’t mean any of them are more real or available than meeting men in your everyday world…. as if that’s entirely possible. The only benefit to online “dating” I can see is that it gives you a chance to be online actually doing something while you are trying to get tired enough to sleep. I am NOT a negative person at all.. I’m just fed up with many years( 31+) of looking for someone wonderful to finish the journey with. Where are all the REAL, grown-up, legally and emotionally available men who have faced reality, gotten over themselves, and learned a thing or two about how to give and receive love???? Maybe I’m asking for too much, but I love and respect myself enough not to just pick any loser and call it having a “man”… or having a “relationship”. I’ve tried OKCupid, Plenty of Fish, Christian Mingle… I’m not sure there is a way to win at this game.

  2. Thank you for sharing this! I loved how you responded to him. It’s good to give people a second chance (or a third) rather than writing them off right away.

  3. Hello Sandy. Bless your heart for wanting to give this offensive man the benefit of the doubt ( and for your curiosity to see how it would play out if you did respond instead of continued ignorance and just writing him off). However,I am leaning a bit on the side of Teddee Graces response with regard to not seeing him as redeeming himself. I would have just left him alone completely because I have found that men such as his type tend to get a thrill out of pushing the envelope so to speak and will always be very good at tossing back a good “sorry” response to keep us in their playing field (yes, a type of control). Its been my experience after nearly 20 years of being single that men show you who they are up front…believe them. I want a man that is classy in the beginning and the end.
    Thanks for all you do.

  4. Thanks, Patty! I do try to give people the benefit of the doubt..until I have evidence to prove otherwise.

  5. I hear you, Robin. And for the most part, it’s true that how someone shows up at the beginning tells you all you need to know about them. However, there are sometimes exceptions to this ‘rule’, and I do like to give people a chance to redeem themselves. I know I’ve said things on dates that were misinterpreted. I would have loved for my dates to have gotten curious instead of putting me in a box.

    Turned out the guy in this article was a jerk, which I confirmed on the first-and last-phone call 🙂

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