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10 Things to Watch Out for When Dating Someone New

By Andrea McGinty July 14, 2023 Dating

My clients range in age from around 48 to 78 years old. I’ve heard many first date encounter stories, and I’d like to share some behaviors that you should absolutely watch out for. Because, let’s face it, if it happened early on, it will only get worse. I like to say, “The best behavior is in the first month(s) of dating.”

#1: Talking on the Phone While on a Date

Daniel, a successful 59-year-old attorney and client of mine, recapped this story for me yesterday. It was his second date with Anna, a pretty, 61-year-old doctor. They’d just had a pleasant tapas/sangria fueled dinner, and he was driving her home.

She took a phone call from her ex-husband in the car, something to do with one of their children. (That’s ok, right?). Well, the small incident was resolved in 5 minutes, but suddenly she blasted into a story with her ex, “Remember when we……” and for the next 20 minutes of the car ride home reminisced with her ex in front of Daniel.

Think there was a 3rd date? And she texted him surprised he never asked her out again.

If it’s not an emergency or a very important call, it can wait. Otherwise, it’s a red flag for disrespect.

#2: Being Nosy

Sure, you can allow a general question about how long you’ve been divorced. But the buck stops there. It’s none of their business at this point why you divorced, was it acrimonious, are you getting alimony, etc.

Mark, 65, told me a woman asked him if he ever cheated on his wife – and this on the first date. He was new to online dating and asked me if that was normal. Heck, no!

#3: Sharing About Having Bad Relationships with Family/Relatives

Maria, 49, had a date last week with Mark over a coffee. Within 10 minutes he had already told her he was estranged from his children as he was never present in their lives. Maria reported to me, “As he began launching into his dysfunctional childhood, I drained my latte and told him this wasn’t going to work, in a gracious manner. And he looked confused.”

He texted her the next day asking what he’d done wrong – and while tempted to tell him, “You need a whole lot of therapy,” she just said she felt no connection. Smart. There is absolutely no reason to stay for an hour when someone launches their issues on you. (Oh, she blocked him on her phone too). Things like this – you just move on!

#4: Language

Regardless of a person’s day-to-day life and habits, foul language – in front of you, on an initial date – is a red flag.

#5: They Don’t Make You Laugh

Many people comment in online profiles that they enjoy a sense of humor. But that can range from silly, goofy, quirky, to a jokester. You either click on this – or don’t!

#6: Gossipy

On a first date? You don’t even know this person. Now, I’m not talking about telling funny stories, I’m talking about a mean-spirited way of describing people. Talking bad about others does not resonate with the majority of people, so take it as a red flag.

#7: Talking Negatively About Your Dating App/Dates You’ve Gone On

Laura, a very positive and happy-go-lucky person (and client of mine) shared this story with me. Her date’s first question was, “Are you finding these dating sites as awful as I am?”

She was surprised, and I liked her answer: “Wow, really. I’ve met some fantastic men – just not the right one for me yet.” And guess what? Even after her comment, he wanted to continue on about all the unattractive women he’d met. She immediately tossed him out of her line-up of potential second dates.

#8: Bad Manners

Christopher, 64, had invited Louisa on a first date to a wine bar for one drink. When he arrived, she was on her second glass of wine and busy ordering not one, but three appetizers. He gave her the benefit of the doubt, but when the check appeared, she left to make a phone call.

Now, Christopher is a gentleman who always pays the check, but he was perplexed when she didn’t even bother saying thank you. And, she had scarfed down most of the appetizers and ordered a third drink too.

Why I’m noting this? Some men do that too.

#9: Drinks Too Much

One drink is enough for a first date. More than that? No!

#10: And the Good Old Being Rude to the Waitstaff

This one definitely shows one’s true colors. Laura, 66, met Thomas, 62, for a second date at Mastro’s, a nice steak house in Newport Beach. (Prior to that, they’d had a pleasant coffee meeting). First, he complained about his salad. But the denouement came when he angrily chastised the waiter about the temperature of his steak and asked to speak to a manager.

Realistically Speaking

Keep in mind that most of the time I hear fun, heart-warming stories about first dates. Sure, not everyone has chemistry, nor is it usually love at first sight. But if you spot the above “red flags” on the first few dates, chances are it will not get better.

My clients who do best and add to my 65% success rate of developing relationships tend to be positive, well-mannered singles. So, keep in mind it only takes one and don’t give up after one bad experience. With 128 million singles alone in the US, I promise he/she may be right around the corner. Chalk it up to experience – and move on to that next date!

And Let Me Cheer You Up

Two of my clients announced their engagements last week. I can’t tell you how happy I am for both of them and their new partners.

Have fun, chin up and just think, you could be next!

Let’s Have a Conversation:

What are some first date red flags that you’ve dealt with? How do you feel about dating sites? You’re your attitude hurt your chances of finding real happiness? If you think you’re better off alone, consider if this is because of past experiences – and maybe give yourself a chance!

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One BIG turn-off for me is a man who chews with his mouth open. Ugh!


That’s why he’s still single!


I am so happy to have these comments to read to get perspective. Very recently I went on a date with a gentleman who told me within 5 minutes of meeting that the last thing has deceased ever said was “you need to find someone new and get married”. We went on 2 subsequent dates, he Talked about his deceased wife on both of those dates. He also never made me laugh as you can imagine because he’s grieving. On the 3rd date I left a bit earlier than he expected I suppose. The next day I Received a text from him saying that I was “Too reserved for him.” Somehow I feel a little bit guilty which is ridiculous. I appreciate the people on here who have such confidence in dating, its inspiring.

Marcia R Corenman

I have found that most men will tell you exactly what is wrong with them in the first 5 minutes. It is called the Lemon Law Disclaimer and the issue is often couched as humor or an anecdote about ‘someone else’ floated to see how you react. Lean into the conversation with tell me more! I’m just curious about blah, blah, blah repeating back what he just told you.

The biggest red flags I’ve heard are: I’ve recently lost a lot of weight, I have an appointment with my Dr. to see if my cancer is back…My ex is crazy and my family won’t let me see my grandchildren…I was recently in an accident with a motorcyclist who was killed, I’d only had one glass of wine…I have a roadbuilding project worth a Billion dollars coming up in Nigeria…My wife is in full time care but I am looking for a committed relationship…I’m using this cane because I fell off my camel…I always wanted to live in San Diego…Need I go on?

I’ve been on over 450 ‘coffee dates’ over 10 years. I’ve heard it all and seen a lot. I wish I could say I’ve met a lot of good men. It was probably where I lived, San Diego,California the land of surfer dudes who never grew up. I”m now in South Carolina, maybe the dating pool is better here.


The same applies to women. I’ve had them telling me all about their estranged families and cancers ad nauseam. It’s not a male thing. It’s a lemon thing.


Two dates pop into my mind. I was meeting one fellow for the first time. His dating profile had indicated a strong interest in antiques, which was also an interest of mine. We met for lunch next to an antique mall. I queried him about the kind of antiques he loved, since the plan was to go to the antique shops after lunch. He hemmed and hawed and finally admitted that he had no interest in antiques but put it on his dating profile because his ex wife loved antiques!
The second gentleman had treated me to a few lovely evenings so I decided to make him lunch at my house. It was on a weekend but he was constantly on his cell phone about work issues. I gently requested that he use his phone after lunch but he became irritated and said he had a job that was 24/7 not 9 to 5. I chose not to see him again. I did not want to ever come second to work, no matter how much a man made. He had commented that he didn’t make “the big bucks” he earned by not being available for work issues at any time. I didn’t care how much he made if he couldn’t take off one hour on a weekend to concentrate on a date instead of his job. It would have been different if it was a work crisis, but there was no crisis, just an ordinary day.

Lisa Stege

Two dates come to mind: the first one monopolized the conversation, and talked on and on about all his possessions and expensive trips to everywhere. The other man talked about his work and hobbies in excruciating detail that could only be interesting to a fellow hobbiest in that field.
I also find it very common that although men like to talk about the kind of work they did, they almost never ask about what I did for a living. I have mentioned this to other women and find that it’s quite common.


The other man talked about his work and hobbies in excruciating detail that could only be interesting to a fellow hobbiest in that field

Sounds like autism

The Author

Andrea McGinty is the founder of It’s Just Lunch dating service. She sold it and founded so she could help singles navigating online dating. In the 2020s, she knows the best way to meet people is through online dating using a professional coach and specializes in singles in their 50s-70s!

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