Dating after Divorce: What NOT to Say on a First Date

Here is more first date input from Don who  wrote about last week. Don, who was one of my first male clients is now back on the market after a seven year relationship and has been keeping me posted on what he encounters. Not your average guy, Don is artistic, sensitive and more in touch with his feminine side. But, don’t kid yourself, he is definitely a guy down to the core.

Below is a list of things women said to him on first dates that me was surprised by.

“Why did you get divorced?”

Of course you’re curious about what happened in his last relationship. But on the first date, focus on the two of you. Don’t talk about your ex and don’t ask about his. On the first date you want to show yourself in the best light and allow him to do the same.

In addition, when you ask about a past marriage or relationship, you can put a damper on the mood, bringing up a sore subject. It’s also a lot like bringing the ex to the date. Why have more than two people on your date? Instead, focus on each other to see if there should be a second date.  On date three or four or five, these things will come out more naturally and both parties will feel more comfortable being vulnerable about what is a very personal question.

Another tip is not to talk about your ex poorly, no matter how awful he was. That is a reflection on you. If he was truly horrible, your date might wonder why you would put up with that or worse yet, see you are an easy target. It’s so much wiser to keep that information to yourself.

“Never been married? What’s wrong with you?”  

I have female dating coaching clients who hate this question. Guess what? Men don’t like it either. Sometimes not ever being married is a sign of commitment issues. Sometimes people were together for 20 years, just never married and both parties were fine with that. You may have judgements about your date, but no need to make them feel bad or critisized by your standards and lack of the full picture.

“Do you own or rent?  Oh, you just rent. You’re throwing your money away.”

Maybe your date has made life choices you don’t agree with. Please keep that to yourself as well. If you don’t, your comments will likely be heard as criticism. And criticizing your date is not the way to his heart. Men choose women who make them feel good, so knocking their choices won’t get you too far.

You may not want to see your date again, but be sensitive to the idea that everyone has a right to their own way of doing things. This way of relating to men will make you a much better date in the long run.

“I have two kids and I don’t know how I’m going to put them through college.”

This is a pressing concern for any person with college age children. But making this statement on the first dates sounds like you are looking to tap into a new source of income. Ladies, please think before you speak! No man or woman wants to feel like your new bank ready for you to make needed withdrawals.

“OK, let’s put the cards on the table. Is this a date? Are we friends or are you looking for more? Me, I’m not sure yet.”

Often my dating coaching clients think they can be direct with men, speaking honestly about how they feel from the first date. Let’s clear that right up – uh NO. Dating is a mating ritual. There’s not much side-stepping – you have to go through the process. There’s no putting your cards on the table right off the bat!

You may want clarity about the date but, think before you speak. How you ask is very important. The funniest thing about this question posed by Don’s date is that she ends by saying she’s not so sure. When the guy asks you to go out and for some reason you feel uncertain if you’re going on a date, that’s when you can  nicely ask him, “Is this a date?”  Nothing wrong with that.

To learn more about undertanding midlife single men, sign up for the Dating for Keeps Expo – a week-long teleconference for women celebrating National Singles Week 9/20-24 – It’s absolutely FREE!


The Check Arrives:

So, what do we do?  Are we splitting this?  Do you want me to figure out my share?  I have a calculator.  How about this- (puts down two tens and a twenty on the table) You can take all of it or part of it.  

I insist on paying my share. Is that OK? 

Single for too long, Ronnie wanted to find love. So, she made a few tweaks and then dated 30 men in 15 months to meet her adorable husband Paul. Discovering the keys to midlife dating, she founded It’s Never Too Late for Love to help other smart, successful women find love too! Her mission is to share her proven dating advice  and keen insights about men with women everywhere who are serious about finding love with the right man. Ronnie Ann Ryan, MBA, CCC is a Certified Coach who has helped 1,000’s of midlife women with her Love & Dating Coach services. She’s been featured on BBC’s 5 Live Radio, NBC, ABC, and Fox News, NPR, eHarmony,,, Connecticut Magazine among others around the world. An established author, you can find her 6 books on Amazon.

2 thoughts on “Dating after Divorce: What NOT to Say on a First Date”

  1. Hi Jeannie – so glad you’ve seen the benefits of not offering to pay. Keep in mind that appearing over-willing or enthusiastic can be a turn off too. It’s human nature to not be attracted to dates who seem too interested too fast. This can appear as desperation- for a man or a woman. So congrats on applying this new wisdom and thanks for sharing!

  2. Wow, I had to learn this the hard way! I’m very used to dining with clients, etc but on a date now I don’t lift a finger nor offer to split or pay anything. If we have been out for several dates then I will offer to split and/or pick up a portion. But NEVER on the first few dates. When I did this (in the beginning of post divorce dating) the message these men got was that I wasn’t interested in them (in fact I was very interested and was trying to show willingness to split costs as things have gotten more expensive)
    Another lesson learned: if a man requests my financial input on a date, he either has serious financial issues or is a serious cheapskate: one guy asked me to pay for movie snacks while he disappeared “to find seats” – this while at a Saturday afternoon matinee!!


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