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5 First Date Mistakes to Avoid, by Ken Solin

 About the Author, Ken Solin:First Date Mistakes by Ken Solin

Ken recently joined Stitch as an advisor and brand ambassador. His passion is helping Stitch members enjoy their best possible online dating experience. Ken has written about senior dating for The Huffington Post, AARP, Maria Shriver, and, for a decade, and the information he shares is based on his dating experiences, and those of thousands of readers who comment on his articles.


First Date Mistakes – We All Make Them!

Whether you’re looking for romance or platonic companionship, the first date can always be a little uncomfortable, even stressful! Even if you date frequently, meeting someone new can be challenging for all of us.

As a general rule of thumb, the simplest way to avoid saying anything embarrassing or inappropriate on a first date is to install a mental, five-second, time delay mechanism in your head, similar to what live television uses to avoid airing expletives. If your date asks you a tough question or makes a challenging comment, that’s the time to engage your time delay mechanism. You need to consider what you say on a first date if you hope to have a second.

Now, with that in mind, here are five first date mistakes to avoid:

1. Avoid Appearing Desperate

“I know this sounds crazy, but I think I’m falling in love with you,” is guarantied to make your first date with this person, your last, because yes, you will appear desperate and crazy. This has actually happened to a few men and women friends, and all of them reacted similarly. Desperate declarations are deal killers. While it’s wonderful to feel excited about someone you met, to suggest a virtually impossible emotional connection is a red flag to all but the desperate. Your time delay mechanism will prevent you from making irrational statements like this.

2. Don’t Suggest Risky Behavior

Suggesting to your boomer date, “Let’s go back to my place and make love,” after knowing him or her for an hour or less, isn’t just crazy, it’s potentially dangerous. And while free love may be reminiscent of the 1960s, it’s totally unacceptable behavior today. A salient point to consider is that if your date agrees to have sex with you, you’ll likely find yourself in more trouble than you bargained for. Casual sex is not new millennium, boomer, dating etiquette.        

3. Don’t Be Combative

Informing a woman on a first date after opening the car door for her, “I won’t be doing this again because the sexes are equal now,” emphasizes the importance of the time delay mechanism. Being a gentleman has nothing to do with women’s equality. It’s simply a gesture of respect. Boomer women appreciate manners and want to feel feminine. Dating isn’t supposed to be a gender power struggle, so don’t make it one. Engage your time delay mechanism.

4. Don’t Ambush Your Date

Planting a surprise kiss on a first date’s lips isn’t even cool if you’re George Clooney or Angelina Jolie. A first kiss is a sweet moment that occurs naturally when a man and a woman look at each other in a manner that suggests a kiss is mutually desired. It’s a memorable moment that couples remember for years. While most people enjoy a pleasant surprise, no one enjoys feeling ambushed.

5. You Can’t Buy Love

Making a show of paying the check for coffee, and adding, “All future lunches and dinners are on me,” isn’t endearing, it’s showing off, and worse, it looks like you’re trying to buy a relationship. In the beginning at least, sharing the check or taking turns paying, makes sense. In that way, no one feels taken for granted or obligated. Once a relationship has developed, a conversation regarding paying for dinners, etc., is appropriate. A successful first date requires balance, not bravado.    

Here is a final tip: Don’t over think being cool.

Just be you.

Don’t try to impress because you won’t be able to maintain that level of behavior. Treat your first date in the same manner you’d like to be treated. Relax and enjoy your first date. It’s supposed to be fun!

If you’d like to ask Ken a question about this topic, please scroll down and leave a comment and he will respond to as many as possible.

31 thoughts on “5 First Date Mistakes to Avoid, by Ken Solin”

  1. OMG! You totally missed things like:
    Grooming! – Clean up those nose and ear hairs. Wear clean clothes.
    Conversation – Avoid telling me about your ex – please!!!!!! And do talk about yourself, but not only yourself – ask questions.
    Eyes – Keep your eyes off the boobs on the face – please!
    TMI – Avoid the TMI – I really don’t want to know about your diseases, bladder problems, or anything else before I even have your name memorized.
    Thank you.

    1. Judith, I couldn’t have said it better. Also, what do you think of someone although very easy to talk to, but NEVER asks you a personal question?

  2. Movies are a bad first choice. How can you get acquainted sitting next to someone in a dark theater. Be punctual and plan to arrive at least 5 minutes early. Suggest a stroll through a park or a beach walk after sharing some kind of food or drink

  3. Guys,

    If your new date lives a distance away, show a little chivalry.
    Don’t put on her WHERE and HOW you might meet up…
    Plan a speific place, and make sure you go the distance, even if you ask
    her to meet you part of teh way.

  4. Why does it say the author is Andrew Dowling and then it says the author Ken Solin? Which one is it?

    1. Hi Ruth,
      Thank you so much for your question – it’s a good one. Ken Solin wrote the article; but the way our blog works, it puts another author as the person who posted his article, which would be Andrew. So sorry for the confusion!

    2. Hi Ruth,

      Ken was the author of the article but I posted it to our blog for him so it shows up as me being the author. Sorry about the confusion — we’re looking at a different solution for blogs and articles which will hopefully mean we won’t have this issue in the future!


  5. Anytime I am meeting someone that I only know from the personals or Stitch, with a photo and a phone call to go on, I’ll only meet them over coffee, especially at a bookstore like Barnes and Noble. This makes it public and helps if they are running late as I can catch up on some magazines or something if there’s any wait time. ; – )

    Then too, it keeps the meeting short as you are there basically to see if the chemistry between strangers works and if it doesn’t you won’t be together for more than about an hour, plus we are all very busy and who has the time to waste.

  6. Dating is a new beginning for both parties leave your past behind and your ex please. Be honest and don’t rush knowing every little detail on the first date. Relax and just be yourself. Windy in Alabama

  7. If men are not interested in sex on the first date (because i am not generally unless undeniable chemistry is present, which is rare indeed) then why do they make references to such why do they think sending a pic of their genitals is pleasing? or a picture of them without a shirt or clothes on exciting? Why do they ask for nudes, bra size, if i wear a bikini, do i like to kiss am i a good kisser, do i like to snuggle? most inappropriate things before you even remember my name and where i am from.

  8. Two horrendous phone calls with women without my even meeting them.

    First case scenario: woman kept sending dozens of photos of her and her friends…did not know which was her…then dozens of photos of her children and grandchildren insisting that I do the same. I could not do that without my children’s permission…and why do it anyway? I ended that connection immediately. Second case scenario: woman asked that before we met if I could still ‘get it up!.

    You then have to understand why they are still looking for men! This is beyond the pale and Ken’s five great ‘first date mistakes.’ Happy being single and writing my ninth book, the topic on dating. It is hysterical. I’ll let you know when it is published.

    1. Jerry, when you finish that book, I totally want to read it! I’ve had some weirdo first dates… Where do some of these people come from!?

      1. Hi Jan
        My answer is, that, that Inter-stellar space is enormous – they may have come from anywhere out there. Scully and Mulder may give you the answers from the X-Files……………

  9. My young adult son and I compared notes about dating. As a millenial, he uses Tinder. Although more than 3 decades apart and different genders, we have the same ideas about what is and is not appropriate. Photos from different eras or vastly different weights aren’t fair to the other party. Misrepresenting educational level, occupation, interests also not cool. Poor grooming, bad manners, filthy jokes, excessive drinking, and sexually aggressive behavior are real turnoffs. Other than that, the best approach is always planning to have fun meeting someone new (in a safe public place) and finding out about them. Even if you don’t hit it off, you might emerge with a good story.

    1. Sue, I quite like it when some people misrepresent themselves (lie), are poorly groomed, tell or send off-coloured jokes, demonstrate racism and discrimination, only talk about themselves, are really late etc because they show who they are straight away and you don’t need to waste any more time on them.

  10. Great reading. Here we go!! Don’t talk about your “Dear John/Jane letter from your ex. Don’t talk about how many men/women that you know. Don’t talk about all of your old flames; that is such a turn off. Keep it simple. If you are comfortable with each other, talking will come easily.

  11. Lots of good thoughts and ideas here…however, I believe the best way forward on a first date…is just be yourself. Don’t pretend to be something that you are not, just to impress the other person. Eventually at some point, the real you will need to step forward (as it is like telling lies. it is just too much hard work and you have to remember what you have said to who, when and where).
    And if people don’t like the real you…well that is okay…as this person would not have been right for you.
    Being honest, truthful and sincere is often a lonely road travelled, though it is a road that I can sleep well each night.

    1. Paul, I like your comment, especially your last sentence, “Being honest, truthful and sincere is often a lonely road travelled, though it is a road that I can sleep well each night.”
      If you don’t mind, I’ll adopt that as my mantra.

  12. Enjoyed your article as well as the comment.
    Sometimes I have a bit of a different take on dating.
    I have been in the dating pool off and on for several years so my prospective isn’t always lined up with those of others.
    Check out my Blog and take a peek on my thoughts. / t / senior-dating

  13. What do you do when you don’t drive? Really don’t want to catch a cab (can be expensive) or ride a bus (takes way to long to get anywhere). I feel so nervous right away cause I’m getting into a car with someone I really don’t know. Am I being too paranoid???

  14. Ken has some very good points; “Put brain into first gear before opening mouth” is a favorite of mine. A little preemptive thought always goes a long way.
    Also, I would avoid too many ‘flattering’ comments. I find these make me feel uncomfortable until I get to know the person. You tend to think, ‘What are they after’ subconsciously.
    And last, but not least, try and keep sex out of the first date conversation, unless your date deliberately asks you a specific question.

  15. Intelligent comments, seems everyone here has had “online” dating experience.
    Will try to keep all those tips on my mind… soon as “someone” out there
    gets interested in my profile….hahahahah Good day to everyone…let’s keep smiling !!!!!

    1. Hi TC, thanks for your question. A lot of our members feel that way so they’re signing up and suggesting other things they want to do in groups. They’ve gone to comedy shows, concerts, movies, brunch, Farmer’s markets, and more! Hope you can meet up with them soon.

  16. I met this Phil Brown at the class- the dance of the 5 Rhythms- He seemed older, kind, nice to talk to but then he had all this ogling look and had a huge crush if that’s what you call it on a married woman- I just thought the chaos entailed wasn’t worth it. Can’t compete with a man who is stretched in different directions. But the dances are his way of finding fresh ‘girls’ I see him sometimes but he was way too senior for me- I do crack up at watching his trying to be sensual and he will dismiss you in the blink of an eye if you don’t give him ‘any’ I am sure if you do give him some he will also not get in touch.Worst first date ever.

  17. Like many of you, I find some of the personal questions asked by some men very strange. What are you wearing is one I hate. My aswer is ‘clothes’. No I’m not going to describe my body in detail. No I don’t want to know about your habits sexual or otherwise. No I don’t want to engage in cybersex. I also don’t like comments like ‘you are so beautiful!’ My standard answer is’no, I’m me being me, being the best me I can be every day’ Honesty goes a long way with me.

  18. I recently met someone over the age of 70 on our first date we had sex and I must admit it was great, however I feel that he only wants casual sex and does not want to be commited. Currently he his out of town and he told me he would call and to date he as not. Please give me your views on the matter

  19. I have done alright meeting someone at parks farmers markets pet shows and a multitude of other places. Im 75 and in pretty good health but I just want companionship! I was an only child and get tired making my own fun!! Joe

  20. Dating at my age (81), is a major challenge to reason when it comes to sex. Some women, (like my ex-wife who are post menopausal) don’t even want to be cudled any more, even if there’s no sex involved. My most recent wife,one horny little cougar, and she too, was post menopausal. Her enthusiasm was based on “No more babies” Jean passed away two years ago, leaving me a widower.

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