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Online Dating Messaging….What a Mess!


This is a date make or break. I can’t believe I have not devoted an entire article to this topic!



You’ve done all this work---hired a dating coach, who wrote an engaging dating profile, have terrific photos, chose the right online dating sites/dating apps….then the bomb drops! You go speechless. Oops, message less. And think perhaps a flower, like, heart will suffice. uh-uh.


Ok, to be clear, I’m not talking about what the other person wrote to you as a first volley---trite things like:

Hey, beautiful! You’re as cute as a bug! Whatcha doing? What’s up this weekend? Happy Monday. I’m normally home most days playing with my Pitbull and addicted to Netflix. Let’s text. (Yes, this is a real one---I bet he has plenty of time to become your long-term text buddy).

(Who votes these are all cuts/pastes?)


But my mantra is: You control the dating process. You needn’t jump on the dates the apps offer you up like a forlorn puppy. You do the choosing. You search. You find him/her. As a dating coach with 25+ years’ experience, I know the time wasters….and the time savers!


Wouldn’t you rather be out golfing or boating than devoting your life to online dating faux pas?


And what does that mean? The messaging ball is in your court! No need to be nervous. You be you.



I had a client who initially was sending texts like this:


Greetings, Harry. I am immersed in my astonishing, yet a bit bewildering globetrotting itinerary for the summer season. My latest tome just arrived at my publisher and she concludes it will be a bestseller. My latest enterprise is fencing which brings me jubilation. Regards, Lynette


OHHHHkkk. This is a 50-year-old woman who laughs on the phone with me---and in general, is quite lovely. When I asked her what’s up with this message (and several other messages to the poor men who received them) she was “astonished” I was questioning her. Lynette, where’s your fun personality and did you use a thesaurus for these?


She told me each response took her 15 minutes to write…. WHATTTTT? Light, easy, breezy, bantering was not found in these. Plus, she was in disbelief no one (not a one!) had responded. Maybe they fell asleep mid-paragraph, I remarked to her. No wonder she told me online dating was depressing and so much work with no rewards.


Ok, what works? This is so easy---read their profile and glance through their photos! Maximum 3 minutes before it’s a delete or a message.


With permission, I’ve taken a SoCal client, Sophia, who recently moved to the East Coast of mine and she’s allowed me to print her opening messages to men---The payoff? This 54-year-old woman goes out now on a minimum of 3 first dates per week and has several in her 2nd and 3rd date rotation.


Sophia’s messages: Yes, she went out on dates with 7 out of 8 of these men. You can see her off-the-cuff style---and in most she referred back to either something he said in his dating profile or one of his photos. She told me it takes her less than 2 minutes to craft a message, doesn’t think too hard, and just goes with her gut. And many men asked her out after the first message---no long text chains that get you nowhere! (Note: the messages are as is; I didn’t correct spelling, punctuation, etc.). I only included a few of the men’s responses to her.


1. HER: You are super cute---as are your dogs! Just moved here from West Coast---where's Clearwater? Not into long distance meets---But I do like the sparkle in your eyes!


2. HER: Hi Peter! Avid reader too----but NYT bestseller fiction---read about 3 books a week.


3. HER: Hi KJ----oh I'm craving oysters right now. Enjoyed your photos! (He was eating a plate of oysters in pic)

His response: Hi Sophia, complimenting my food...you know just how to melt me. : ) Not sure when you will see this. Would you like to meet for coffee Saturday before noon? If so, text me tomorrow at xxx-xxx-xxxx Ken


4. HER: Enjoyed your photos---you have a great smile and can tell you love your family! I have 6 siblings---so totally get that!

His response: We are definitely on the same page ! I'd definitely like to meet you. Perhaps an easy breezy hello drink and talk a while. I’m ready !! Please feel free to leave me your cell. Or send a hello test if you feel comfortable. Hope so. Xxx-xxx-xxxx Bill


5. HER: Darling dog! I have a sweet 3 y.o. golden retriever.

His response: Hi Sophia. Alvin is my daughter's dog but we share custody lol. She's leaving for a work trip today so I'll have him all week. I'm sure everyone tells you but you have a great smile. Lunch would be great. I am flying up to NJ today for a funeral. Working on a flight back. What day(s) work for you? Michael


6. HER: Ahhhh, I’m a Pickleball newbie started 3 weeks ago and just love it!


7. HER: Hi----great photos, I felt the story of your life! Traveling and sports are biggies---have a new recent addiction to pickleball and can't seem to leave the court! I have two teen girls---one a senior like yours and one a junior. Recent Ca transplant!


8. HER: Oh I'm in love with pickleball---taking a semi-private this morning at BR Tennis Club--never played tennis but my dad was a champion ping pong player while stationed in Germany in army so we played a lot as kids! I started playing a month ago---playing low intermediate now and have a competitive streak so it's fun to find a new sport to love. I tried golf when I first retired at 43 and was never so bored in my life. Turn arounds can be fun---as long as well-funded, right? Where do you play?


His response: Hi Sophia. You truly caught my attention. You seem like an all together, well grounded class act woman. Really like your positive outlook on life, Friends family and the future. We seem to share many of yen same views, values and wants in life and in a relationship. I play at PB Club. Please take a moment and check me out and please read my words. It would be super to get a positive response from you soon. Lunch Thursday or Friday? Thank you for your time. William


You be you! It works. I just got off the phone with a Chicago client—he, too, complained of lack of dates. So, we crafted messages together for 45 minutes together---sent them and toward the end of our call---he has a 5pm drink date today on Rush Street!




Love & Laughter,



Andrea McGinty (Your Dating Coach!)


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