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Dating 101 Presents: First Date Red Flags

Updated: Jan 21

How to tell if your date is one for the history books, or one for the Apologies I Never Got book. When to just say no to that second date.



Due to recent events, many people are finding themselves hurled back into the world of dating, some even for the very first time! For those who married their first loves, or got married right out of college, they may not have had to navigate the turbulent seas of the adult dating world before or if they have, it’s been a while.

Which is why Of Martinis and Men presents: Dating 101. A quick crash course on entering or re-entering the adult dating world. For today’s topic we are going to cover First Date Red Flags. Here’s the thing, the person doesn’t have to burst into tears, go to the bathroom and never come back, or show you pictures of their 10 kids from previous marriages for you to know the date isn’t going well (although please tell me those things might set off some alarm bells.) The art of dating is often more subtle than that. A lot of knowing whether a date went well or not…is based on your own intuition. But just to help tweak that intuition in the right direction, I have outlined three sure fire red flags below.

Talking About an Ex — We have all dated before. Which means we all have ex’s; ex partner’s, ex-spouses, ex people we went on a few dates with. Most of us have had dating and relationship scenarios that did not go well or did not end well. But here’s the good news on them, they are over. There is no need to rehash them to anyone willing (or unwilling) to listen or to take out the ex’s mistakes on a new, innocent partner.

Because ultimately our healing is our own responsibility, regardless of what the other person did or not do. I know, that doesn’t seem fair. But think about it, we can’t just walk around taking out our pain on others, because I guarantee someone has had it worse than you, so where would we draw the line? Who would determine if you being cheated on was worse than someone else being stolen from? We couldn’t, and that’s the point. We have to be in charge of our own healing. The past is the past and that is where it belongs, not strewn across the fancy restaurant table on a first date. So, if the person sitting across from you is spewing all kinds of venom or comparisons about their ex’s or even just repeatedly bringing them up, that is not a good sign. Among other things, it is usually sign that they are not over it. Not necessarily that they want to get back with the ex, although that may actually be the case, (remember the opposite of love is not hate.) It might just mean they are not over the energy of the relationship or over the emotional wounds it left.

Which is not to say they are terrible, awful people, it just means maybe they need some time to work through it, without tossing in all the emotions a new relationship brings. It is their wounds to heal, and it is not your job to prove that “you are different” than their ex, or to make up for all their ex’s shortcomings. Who wants to start a relationship, in the shadow of an ex? Good or bad. It is usually just an indication that the person sitting across the table from you, is not ready for a relationship, regardless of what they may be claiming. It really is better to just steer clear of ex chummed waters.

And speaking of…the same may go for you. If you find yourself harboring some ex resentment, or bringing them up a lot, especially when out of context, you might want to take above advice and give yourself a few months to let some of it go. For example, if your date says “Oh I love shrimp” and you find yourself saying “My ex hated shrimp.” Ok…great story Hemingway. Were you planning on selling the movie rights to that or what? Basically why…just why. It’s not necessary and is a sure fire conversation halter. Or worse, they feign interest, and it sets you off down a rabbit hole of how your ex never appreciated all the money you spent buying them shrimp or the time you spent cooking them shrimp etc. BORING. And AWKWARD. It would be around that time I would be asking for the check. So to recap, no one’s ex’s should be a topic of conversation on a first date. If they are, consider giving yourself or the other person some space to work through it.

Laying Their Burdens At Your Feet — We all have something. Whether its awful ex’s, rough childhoods, tough life experiences, financial, health problems or all of the above! But there is a difference between it being presented, and someone laying it at your feet.

Sometimes that difference is subtle, energetic. Do you leave the date/conversation feeling drained? Do you feel tired or emotionally exhausted? Annoyed? Unheard? Did their problems take up the entire date or conversation? These are the red flags. It is perfectly acceptable to disclose something they feel is important for you to know on a first date. It is something else to be turned into their therapist. For example, I was asked out by a guy I knew through work. We had had some light conversations, felt some mutual attraction and he had asked for my phone number. Through the texts I immediately felt overwhelmed. He went into great detail about his emotional and mental health issues, how they had affected his eating and sleeping, how it created crippling depression and how no therapist had been helpful etc. I found myself offering solutions then realized I was starting to feel obligated.…a huge red flag. This was far too much information off the bat, and I was quickly turning into this guy’s therapist and remember we hadn’t even been on a first date yet! I began slowly backing off, I responded less to his messages, did not involve myself in the problems, and eventually cut him off completely, even before our first date. Because therein lies the difference between being open and vulnerable, and someone laying their problems at your feet.

Think of this as a soft interview with a job, you are getting a very basic idea if this is a fit for you. It is figuring out if you are even generally compatible on mental, physical and emotional levels. Most of the conversation will center on surface topics, as it generally should. Not that you can’t go deeper if you are feeling a connection but ideally the second and third dates are more of the platform for vulnerable conversation. Some things the other person just doesn’t need to know, it’s too much information for a first date. It’s honestly like walking up to a stranger and telling them about your Athletes foot problem. It’s generally uncomfortable and not entirely necessary. And for all intents and purposes, this person is a stranger. You might walk away from this date and never talk to this person again. So, telling them all your troubling dark family secrets, or all your deepest insecurities about your back acne, just might not be appropriate.

Not only is not necessary but it can also be indicative of someone not having their life together. It is a first date, they should not be asking you for anything except maybe a second date if things go well. But if they are showing up to the date and asking you to pay because they don’t have any money, or asking you to chauffer them to some errands because their car got repossessed or asking you to diagnose their mental health disorder, I think you can begin to see where the problem is. They are showing you a red flag that they just do not have their life together right now and it is probably not a good time to be dating. You will end up in a relationship and situation that will make you feel used and drained. Best to steer clear.

You Feel Uncomfortable- Whether its them not walking you to your car, talking badly about their ex, being rude to the waiter, showing up late with no apology or whether it’s just a general feeling of ick that you maybe can’t even put your finger on, it’s a NO. Remember this is a first date, a free trial and if you want to cancel your subscription to this person, you have that right, at any time, no questions asked. You do not owe them anything; not a second date, not a validation of why, a simple “I’m not interested in a second date” will more than suffice. Whatever reason you have…I assure you it is valid. They don’t have to agree with you, they don’t even have to know what your reasoning is if you don’t want to share it. And remember..a feeling is VALID. Even if you don’t have a concrete example, your intuition is your best friend in navigating the dating realm.

I’ll give you an example, I was once on a first date with a guy, that had started out pretty well. He was smart, funny, generally attractive, no initial obvious red flags. We began a discussion about dating apps and he had asked if I had ever been catfished before. If you don’t know what that is, it is where someone presents themselves differently online than they are in person, so like they post pictures from 20 years ago, or say they are CEO of a company but are unemployed etc. I told him I had never had that happen and he began telling me about how he met two girls from the site who ended up being “so much fatter” than their pictures. He went on and on about how disgusted he had been and how upsetting it was. The way he talked about the women, and their bodies, completely turned me off. He was so disrespectful about their weight and their appearance, that it made me uncomfortable. What had begun as a funny anecdotal story had quickly taken a very dark turn. It continued even past the point of me trying to change the subject. That was the end of that. While he wasn’t talking about me, and hadn’t used any classic derogatory terms, the way he was talking about it made me very uncomfortable, and that was all I needed to know.

Pay attention to your instincts, they are there for a reason. If you don’t like how the girl is talking about how she only dates wealthy guys, that’s a flag, if the guy says he won’t date girls over a certain weight, there’s a flag. If someone is rude to the waiter, doesn’t walk you to your car, says cruel things about a gender, religious group, or race.. If it makes you uncomfortable, regardless of what it is…that’s a RED FLAG. It’s honestly not even worth giving it a second date at that point, there’s no reason to waste everyone’s time and there’s no reason to put yourself in at most volatile and at minimum awkward situation.

So long story short here’s how it should look: You go out, you grab some coffee or dinner, you get to know things about each other like where there from, what they like to do for fun, what they do for work, if they have kids, siblings, etc. You have some laughs(hopefully) and you part ways, maybe with a hug and kiss and with no one being left standing alone on a dark city street. Let me be clear, if the night ends in tears or dark family secret confessions, if you now know more about their ex than you do about your own, if you find yourself googling numbers for the local AA or anger management chapter for them, if you feel like there is not enough sage or therapy sessions in the world to cleanse you, and if you feel relief at getting away from them…you have just experienced a bad date my friend. Recognize the red flags, cut your losses, and move on to a date that has a few less warning signs and a few more green lights.

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