First Date Tips: Dating Red Flags

First-Date-TipsIt’s been a crazy few weeks. I’ve not only been super busy with work, there’s my blog, my business and the podcast.  Wow, crazy.  But, I love every minute of it. You might be wondering how I find time for dating but I do. Actually, I love meeting new people and I’ve gone on a lot of first dates lately.  Yes, lots of first dates that didn’t go anywhere else for whatever reason, mostly because we didn’t have a connection and that’s perfectly OK. Others I would have loved to see again but it wasn’t in the cards. That’s perfectly OK too, just because you felt a connection doesn’t mean they did.

People put too much pressure on a first date when really it’s just that first contact to see if you want to proceed to the next level, a “pre-date” if you will.  That’s why coffee or a drink or a nice walk somewhere is the best option. Anyway, we’re here to talk about First Date Tips, in particular Dating Red Flags.  So here are some of the characters I’ve been on a first date with in recent history … recognize any? Most apply to both men and women. Would you add to the list?

First Date Tips: Dating Red Flags

Liar / Exaggerator

This is the person that lied in their dating profile. Their picture doesn’t look like them or they exaggerated their qualities.  I had one guy show up twice as heavy as he looked in his picture but apparently it was OK, I wasn’t to worry because he was going to have gastric bypass surgery. Uh-huh.  I also had another guy who looked nothing like his picture, when he showed up I was surprised and then asked him why he didn’t put up his own picture and he said that it was his cousin’s picture because he didn’t want people to know he was online. That was my cue to leave.

Why it’s a dating red flag:  Obviously it’s a red flag because they lied upfront and will most certainly lie again. No doubt about it. Misrepresenting yourself online is a big offense in the dating world. What do these people think? That no one will ever find out? Geez.


So this person is a little too touchy feely.  Light touching of arms, hands back is OK.  Going for the boob is NOT OK! Any unsolicited touching shouldn’t be on the table on a first date unless that’s something you both want to pursue.

Why it’s a dating red flag: Well, more often than not, this person isn’t interested in something serious with you. If that’s all you want too then go for it, but if you really want a relationship then keep it in your pants.

Already Planned Wedding

This person already has their life planned out and are interviewing candidates for happily ever after.  If you encounter this RUN! You know why? Because they won’t see you past your spouse potential.

Why it’s a dating red flag: They usually aren’t authentic and will act how they feel they need to act to get what they want. It will all be about getting married and rarely about the actual relationship and how you are as a couple. You need someone who is looking for a companion not a spouse.

Creepy Eyes

That happens to me sometimes, they just stare at you and it’s unsettling. Shifty eyes are also creepy. I had one guy bulge his eyes at me while staring and telling me I’m beautiful. Trust me I couldn’t get out of there fast enough.

Why it’s a dating red flag: Eyes and eye contact will tell you a lot about someone, do they look at you while you’re talking or at everything else going on? Do they stare at the floor when they talk? Do they stare at you with a blank look in their eyes? There is normal looking and abnormal. If it makes you uncomfortable then this person’s not for you.


The person who tells you their life story in one sitting is problematic. Especially when this person is complaining about their job and their life and their ex and everything else wrong with the world. The overshare is never appropriate for a first date.

Why it’s a dating red flag: Don’t they have something more interesting to talk about? Not only do you leave nothing to the imagination or to talk about next time, you also show that you’ve got unresolved issues. When someone more than mentions an ex in passing then I know there is some baggage there. I had a date recently that when I left I realized we hadn’t even really talked about our personal lives, we had such a great discussion about other stuff that it didn’t matter. Now THAT is a good date.

El Cheapo

Someone who is cheap on the first date will always be cheap. If a guy doesn’t offer to buy you coffee or whatever you had then keep moving. That’s why I say coffee or a drink is always the best option for a first date, girls shouldn’t be greedy either and order the most expensive thing on the menu! Guys, even if a girl offers to pay or split the bill on the first date DON’T ACCEPT!!

Why it’s a dating red flag: First dates are when people are trying to make their best impression in order to get another date, if someone shows they are cheap on the first date then it’s not going to change. Same goes for greedy people, if someone comes off as money hungry the first date then keep walking.

narcissistThe Narcissist

Well, when your date spends the whole time speaking about themselves and THEIR accomplishments and THEIR life and how great THEY are, just keep walking and don’t look back.

Why it’s a dating red flag: You obviously don’t want to be with someone more interested in themselves than you. Conversation should be balanced and interactive.

Tell me about your first date red flags! I would love to hear about them in the comments!

Your Sister in Dating Bliss,

Single Dating Diva

Copyright Single Dating Diva


  1. I always end up with “El Cheapo” and it is such a pet peeve! I grew up in a generous household where we left appropriate tips. I dated a guy where I’d always throw in a few extra bucks when he wasn’t looking because I knew he wasn’t leaving enough. Ugh. And the “oversharer.” Sadly, sometimes that’s me!


      • I think it’s part date anxiety and part not wanting to be perceived as hiding something. This is something I struggle with also. I don’t how many times on a first date I’ve revealed something then immediately regretted it. But I’m getting better. I find taking a second to pause before answering anything is a good strategy.


  2. The only point I have to STRONGLY disagree with you on is El Cheapo. Yes, a cheap person is problem. I don’t like them. You don’t like them. Nobody likes them.

    But there is a huge difference between that and saying that the guy should pay for your first date. Doesn’t that just make the woman “El Cheapo”? The real El Cheapo is the person who stiffs the tip (or under-tips as singlesassy mentioned). If I invite you out for a coffee, I’m going to try to pay (regardless if it’s a date, you’re a friend, or whatever). If a woman invites me out for a coffee and then stands there and expect me to pay for her, that makes her El Cheapo and she won’t be seeing me again. I won’t be used as a cash machine.


    • Thanks Todd. Expecting a guy to pay for a first date has nothing to do with a woman being cheap or not. I have very gladly paid for future dates, but paying for the first date is just the gentlemanly thing to do. Call me a traditionalist or old-fashioned, but that’s how I feel and I’m not the only one. Most women feel the same way. I never order more than a regular coffee or tea or one glass of wine, I’m not looking to take advantage of anyone or use them as a “cash machine”. That’s a little extreme don’t you think? But if a guy doesn’t pay, especially if the bill is $2, it tells me something about him. If that doesn’t work for you then that’s OK, everyone has to do what works for them right?


      • I see it very differently. Offering to pay for yourself is the polite thing to do, no matter what collection of squeezy-fun-bits you happened to be born with. As I said, if I ask someone out, I’m going to pick up the bill, not because I’m a man – because I’m a nice person. If they don’t even make a token effort to contribute then I see a huge red flag – because nice people offer to buy their own coffee even when it isn’t expected of them.

        Don’t get me wrong, I do see your point. But, if we base things on “tradition”, shouldn’t it be the man’s job to pay for dates? Always? And shouldn’t the woman stay at home and raise the kids? Always? And what’s with all this newfangled automobile nonsense – horse & buggy did just fine! Not all traditions are correct in the modern world where we are supposed to be equals.


        • Fair enough … but men and women ARE different! We can’t pretend that we’re equal because we’re not nor should we be … but that’s another story;) Agree to disagree on this one Todd?


  3. Let me throw this into the mix for red flags – because this is an absolute deal breaker for me. Rude to the serving staff at a restaurant. This person either feels they are above the server, or just doesn’t generally know how to behave in public, and neither of those are qualities I’m looking for. 🙂


  4. A big red flag for me is if he shows signs of road rage while driving. Unfortunately this might not come out until after you’ve had a few dates. But be aware of it. Not a good sign…


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