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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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Shirley Deepsong

When a man only talks about himself or if he asks you a question but clearly doesn’t listen to your answer and goes right back to talking about himself.

Stephanie Bryant

So how do I get someone to help me find the perfect guy without doing online dating? I’m from old school and I want to meet someone organically as I’m usually pretty good judging them pretty quickly. But now at the gym, everybody wears earbuds, nobody goes to dance clubs anymore and certainly nobody seems to talk at the grocery store or checkout line. Very disconcerting!

Gerry

I’m 65 and my wife of 40 years died a year ago. Initially I tried dating apps but soon became disillusioned. I’m wealthy, healthy and slim, and looking for a slightly younger woman to accompany me on world travel. No takers, but lots of game-players and people who are totally focused on themselves.

Eventually I gave up and now I’m trying to be happy living alone. Some days are fine, some days are hard. I have moments of great happiness. I have total freedom, living an isolated life. My son lives on the other side of the world. We talk every day. I have some friends living far away and we exchange emails. It will have to suffice.

The US Census Bureau estimates that each year, out of every 1,000 widowed men and women ages 65 and older, only 3 women (0.3%) and 17 (1.7%) men remarry (Clarke, 1995).

Tata

Gerry you are young, do not give up! I read recently, ” when men marry, their risk of death decreases, thanks in part to their wives’ support and social connections. another quote being deeply loved by someone gives you strength, while loving someone deeply gives you courage” Lao Tzu

Best to you….

Cheri

I’m divorced and was on dating sites as well..I have a trust issue with men, not believing they are authentic. Been with myself after giving up and I’m satisfied most of the time and spending time with friends and family! At times like the holidays, it would be nice to have that special person, not necessarily a husband to do things with.. My question to you Jerry is: why would anyone agree to take this awesome adventure on without knowing you ….isn’t that unrealistic?

Anna

And what about people who only talk about themselves…..

Jan

That describes most of the men that I have met. Zero conversational skills, zero interest in getting to know another person

The Author

Andrea McGinty is the founder of It’s Just Lunch dating service. She sold it and founded 33000Dates.com 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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