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10 Red Flags on the First 3 Dates

By Andrea McGinty September 13, 2023 Dating

Sometimes you won’t see a red flag on the first date. Both parties are on their best behavior and the date is just great. But, by date 3, you can generally see if there are some issues that will be future date breakers. After over 25+ years as a dating coach providing online dating services, you’d be surprised by what I see popping on dates 2 and 3.

Here’s a list of 10 to pay attention to:

Right Person, Wrong Time

Darn it, it happens! You may have met the right man – but he just finished a long divorce or is recovering from being widowed. She may be the right woman – but she’s stressed with a new job, caring for an ailing parent, or just had a major event in her life such as moving or a death. Six months in the future this person might be the “one,” but they are not the “right one now.”

No Follow Through

Haven’t we all had that first date where we just clicked and made plans for a second date? Then… nothing. You don’t hear from him for weeks; when you do, it’s a lame excuse. Or you made plans for a game of tennis and an hour before, he cancels – with no reason. Consistency builds trust and trust builds a relationship.

No Questions

You’re both attracted to each other – and all he does is talk, talk, talk. About himself. His work. His golf game. Asks you no questions. Let’s say this occurred on Date #1. Date #2 begins in the same fashion. What would I advise? Graciously cut into the conversation with a “Wow, Michael, I feel like I know so much about you. Ok, so what would you like to know about me? Fire away.” If he doesn’t get the hint, adios.


Oh, what fun is this! Major sign of negativity and who needs this? Whether he’s venting about online dating (run), his son’s college tuition and how the ex pays nothing, the ex, the weather – well, he is showing his true colors. Maybe he’s having a bad day, you may think. Nope, that’s just an excuse.

Don’t we all want positivity in our lives? If this is the beginning of a potential relationship, just imagine how much worse it will get. I don’t care how good looking he (or she) is!


There is no eye contact. He’s playing with his cell phone. Looking around the room. Looking at his watch. Asking you to repeat a question. I could go on and on with this one.


They are being evasive about basic questions like what they do professionally, family, where they live. Now, I don’t mean you should be asking super personal questions like “When did your last relationship end?” or “Are you looking for a long-term relationship?” as those are inappropriate for the first couple of dates. I’m thinking right now of some of my clients that are in long-term relationships – the first few dates were common interests, current events, travel, etc.

Constant Texting

Lara, a 62-year-old client of mine, really liked Chris after the first two dates. But then he began texting constantly – every few hours. As an ER doc, it annoyed her. She asked him not to text during the day. You know his response? “I miss you.” Needy, I daresay, and she correctly moved on – and is dating happily a “normal” texter!

Hot and Cold

One moment warm, the next they’ve forgotten about you, seemingly.

Can’t Plan Anything

Two facets to this one:

a. Great first date. Then endless texting and he/she can’t plan anything because of a bunch of insipid excuses – work’s really busy, they have a seminar just that weekend, their friend is in town, they’ll get back to you. This is not what you want – so don’t put up with this. Move on.

b. It’s the 2020s. To be fair, it’s up to both people to come up with fun dating ideas. He might suggest bike riding – as my client Hunter did on his date on Saturday. They rode over 14 bridges in NYC and had a blast. His date suggested a trivia night this week. The worst? “What would you like to do” to be answered with “Oh, I’m easy – you pick.”

Talks About Money

Rich man, poor man. Either way, boasting of how much you make, your toys, your 5-star vacations just makes you look insecure. On the other hand, “I’m underpaid,” “My wife took all in the divorce,” “My ex refuses to pay child support,” etc. all are inappropriate and very good signals to move on.

Let’s Have a Conversation:

What are big red flags you noticed on the first three dates? What are some green flags on the first 3 dates that gave you comfort and confidence?

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Viktoria Pettypiece

First date,just a coffee to meet, rude to the waiter, turned me off right away… got talking about what we wanted in a relationship, I kinda hinted that I really need to get to know someone before any real intimacy , he didn’t listen and was way too touchy feely. Not for me !!!! Felt he was only interested in his own needs


Our first phone call went really well, he is on the west coast and I’m the east. For our second phone call, I set my alarm to call him when he got off from work (recording music, trying to set up a tour and so on) he didn’t say thank you after I woke up two hours before my alarm to talk to him…and that was only one item..never asked about my work or how my day was, the conversation seemed one sided.

Lynne Stevens

Our first romantic weekend together, a wine tasting in Santa Barbara County, we came downstairs to the restaurant for breakfast. He spent the entire time reading a newspaper. It was embarrassing and awkward. He seemed completely unaware that it wasn’t okay. Needless to say, he was history after the first weekend.

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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