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The Subtle and Not-So-Subtle Red Flags of Online Dating

Alice in Wonderland
8 min readJun 18, 2020


Most of us are aware of the horror stories of online dating and the peculiar, goofy, and sometimes creepy men that are out there. There are obvious red flags we should heed but more importantly, there are also subtle red flags to take note of before considering moving forward with someone. You are probably well aware by now of the more obvious red flags from the many articles written on the subject, your own experience, or from the stories of your single friends as it has become more and more commonplace to lament to your girlfriends in weekly bitch sessions on the lack of “normal” single men out there on the dating apps. Myself included. But fear not, there are good men out there and you shouldn’t waste your time on the ones who are not. By being aware of red flags that ultimately will lead to heartache and time wasted, you can weed out the less desirables and leave room for the man you deserve.

By red flags, I’m not referring to those profile annoyances that should have weeded a lot of the less desirable men out in the first place. These annoyances include but are certainly not limited to men who post:

  1. Shirtless muscle-flexing selfies taken through a bathroom mirror
  2. Selfies in bed in a come-hither pose (Gross!)
  3. Multiple profile pictures with several people posing, skiing, golfing in the distance so you can’t see the man’s face or discern which one he is in the photos
  4. Pictures of pets, children, grandma, and of random scenic sites, but none of him
  5. Profile descriptions that include acronyms to describe himself like DTE (down to earth), LS (legally separated), ESTJ (extrovert, sensing, thinking, judging), WWA (will answer all), and SD (social drinker) to name a few of the least crazy ones I’ve seen. Sprinkle in a few emojis with the acronyms and you end up with a profile description that looks like a foreign language or something a toddler would scribble together.

Then there are the glaringly obvious red flags that if these men were not weeded out with those profile annoyances, you surely will kick them to the curb now:

  1. Has had multiple marriages and shows a lack of responsibility. A man who has had multiple divorces is a red flag in and of itself but when he also adds that his multiple marriages didn’t work out because the women were all crazy, well, that’s a double whammy red flag.
  2. Talks nonstop about himself. A man that talks nonstop about himself and never asks about you or if he does ask about you, he cuts you off mid-answer to continue to talk about himself, is someone who leans on the narcissistic side of the street and hasn’t realized yet (and probably never will) that he isn’t the center of everyone’s universe as he is in his own.
  3. Moves too quickly. This man calls you sweetheart after the first date, tells you he loves you after two weeks, and incessantly texts you morning and night that he misses you when you aren’t together. Not only is a desperately needy and clingy man a turn-off, he will also undoubtedly try to control your life in his quest to make himself the center of yours, and in turn, you run the risk of losing your identity to the relationship in an endless and futile quest to please him.
  4. Shows up disheveled. This man shows up to your date looking disheveled, unkempt with stains on his clothes and holes in his socks. If a man walks into your first date looking like he hasn’t taken a shower in weeks, glanced in the mirror on his way out the door, or done laundry in a decade (yes, this did indeed happen), then good lord, what does he look like when he isn’t on a date?
  5. Admits to mental illness. No need to explain this one in too much detail but you have to appreciate the guy who tells you about his diagnosed mental illness upfront. I was on a date once with a man who did not drink alcohol. I asked what lead him to decide to stop drinking and he proceeded to tell me that he was diagnosed with paranoid schizophrenia in his twenties and that his drinking exacerbated his paranoia. Hmmm.

Now we get to those less subtle red flags that are initially easy to explain away or dismiss, but instead should be heeded and explored further. These red flags are not typically revealed in a profile and generally speaking, are only touched upon in a first meet-up but certainly warrant a deeper dive:

  1. Inability to talk about his feelings (aka emotionally unavailable). This man changes the subject or dismisses it altogether when the conversation becomes uncomfortable or too personal. This man sticks to the mundane and the superficial even after several weeks or months of dating. I mean you can only talk about the weather so long, right? But seriously, a relationship with an emotionally unavailable man is a very lonely place indeed because a big part of developing a deep connection with someone is the ability to be vulnerable.
  2. Not close with his children. I am wary of a man who has no relationship with his children especially if it has been many years since his divorce. I dated a man briefly who told me he had no relationship with his son because, in his words, the son sided with his ex-wife and had become disrespectful towards him. And for that, this man walked away from his son altogether. While it may be true that his son had become disrespectful toward his dad, it’s important to dig a little deeper. What is also important and very telling is what this is doing about improving his relationship with his son now? Is he trying? Does he reach out? or is he indifferent and uncaring? It turns out this man had had a two-year affair with an office co-worker and walked out on his family to pursue a relationship with the woman, blindsiding and devastating his family in the process.
  3. Lives with his parents. I met a man who told me he moved in with his parents after his divorce to get on his feet. Only his divorce was six years prior. While it’s certainly not uncommon for a man to move in with family temporarily after a divorce to figure things out, a grown man living with his parents for years on end is not only a turn-off, but worrisome. Turns out this guy was a alcoholic and had lost his job and marriage because of it.
  4. Has rigid routines and odd pet peeves. A man who says he religiously clips his nails every Sunday at exactly 11:45 a.m. right before lunch or has a pet peeve with multiples of 5 or dishes not washed immediately after dinner raises the ol’ OCD flag. After two dates a man I had been seeing invited me to dinner at his place. I liked him thus far and thought it was a nice gesture and another way to get to know him better. And I was right. When I arrived at his place it was spotless and lovely and unlike any bachelor pad I had seen. He was busy making our dinner when I arrived, from scratch I might add, homemade mashed potatoes with garlic butter and filet mignon in a red wine and balsamic sauce. Impressive. When dinner was ready he had me sit on the far end of a long table that sat 12 and he sat on the other end. A bit awkward, but okay. Within about ten minutes of sitting down to eat (he actually didn’t eat his food as much as he inhaled it), he was in the kitchen doing the dishes. I hadn’t even finished half my dinner and I never did finish because I ended up following him into the kitchen with my plate which he promptly took from me to load into the dishwasher. Over the next 20 minutes he cleaned the entire kitchen including mopping the floors as I sat awkwardly at the island and watched. He was silent, intent, and focused as he cleaned and scrubbed and I was soon out the door. Just a little OCD, you think?
  5. Treats his daughters like girlfriends. There is nothing wrong with a father financially supporting his daughters and showering them with gifts once in a while but when these daughters are 23 and 26 still living at home and incapable of making decisions for themselves or holding down a job for longer than a week, you have to wonder about the dynamics at play. This particular man, adopted when he was an infant, was doing just that. He would send them flowers along with those he sent to me, bought them matching BMWs, they joined us on dates and had a say in everything. I quickly realized that these girls were taking advantage of their dad and his need to quell what I assumed were abandonment issues and create a financial dependency with his daughters to ensure they would never leave him. But I soon did, unwilling to settle as girlfriend #3.
  6. The Cheapskate and unromantic. A woman wants to feel special. A woman wants to know that her partner has taken the time to get to know her and that he feels she is worth the extra effort and the money. I dated a man who was quite a sweet man but couldn’t bring himself to do anything special for me that required any thought or effort. For my 50th birthday he brought me a half a dozen donuts (not even a full dozen), a stick balloon purchased at the grocery store check-out line (I wasn’t even worth the cost of a mylar balloon) and the get-one-free of his BOGO Find Your Ancestry Kit he purchased for himself (sigh). Nothing like having to tell your friends THAT one.

Of course, there is no magic formula to finding the right man online but if there was it would not be: bathroom selfie + emotionally unavailable + narcissist = successful relationship. You do, however, have red flags both subtle and not-so-subtle to raise your antenna and explore further. Some are no brainers and should immediately prompt you to end your pursuit right then and there and others should be met with caution and further conversation.

If you are serious about finding that forever partner then these red flags should be viewed as clues to who a man is, what he is all about, and a glimpse into what a long term relationship with him may look like.

As Maya Angelou so wisely said, “When someone shows you who they are, believe them the first time.”