Note: this is is the third installment of Dating Week, a series of blog posts sparked by a discussion last Saturday with two other single male friends.

The physical manifestation of my dating history.

Although meeting women when they’re out with friends isn’t the best time to pick them up, it does have its benefits. They tend to be more open, more comfortable, and more themselves. You can get a better idea of their true personality, quirks and all.

Quirks aren’t necessary a bad thing. I want  a woman with a lot of personality. As such, I’d like her to feel free to be herself; fully unrestrained, fun, and at her most unguarded.

There are quirks, but then there are red flags. Being able to decipher the difference is an important skill that I’m a long way from mastering.

I probably don’t have to explain what a Red Flag is, but just in case: a Red Flag is a euphemism for a warning sign. In other words, say you’re on a first date and all a woman can talk about is her ex-boyfriend. That’s a red flag. Another example: you go out to dinner and the person you’re with gets tipsy before your food hits the table. Major red flag.

My personal favorite red flag story: I was on a date with a woman I had met through mutual friends. Due to the company, both of us were comfortable and relaxed andhit it off well. We made a date for the next week, which also went well…to a point. There were a few moments and statements made that gave me some pause, but with my propensity for missing those little red flags, I didn’t pay them much mind. Thankfully, she had a flag the size of a football stadium to unveil.

As we were discussing our respective pasts, she brought up her engagement a few years back. It was sort of a sad story, as she was practically left at the Altar. At the moment, I didn’t think too much of it. Again, I’m an idiot, but something like that is certainly an important and traumatic experience. I mean, it’s bound to come up at some point.

Then we moved onto another subject, and it came up again…and again.

And again.

The kicker came later in the evening. We had moved on to an entirely different subject when she, without warning, emptied the contents of her purse onto the table. It made me literally stop mid-sentence. From the pile of assorted materials she took out a folded up page of a magazine, opened it, and handed it to me. It was an advertisement for a bridal gown designed by…someone. I forget whom, and I most likely didn’t know who they were anyway.

What a guy doesn't want to see on a first date. Well, the woman's fine, just not the dress.

“What’s this?” I asked innocently.

“That,” she said, “is the gown I would have worn.”

“And…you carry this everywhere with you?”

“For the last three years.”

If there was an alarm that went off whenever it was time to finish up a date and cease all romantic pursuits, it would’ve caused dogs on the other side of the city to howl. All in all, nice girl, but holy crap.

I thanked her at the end of the date. Not insincerely, either. Sure, I was thankful that she was forthright about something that was weighing far too heavily on her mind to be anything but a detriment to any potential relationship rather than an enchanting evening, but at least I took something out of it. I’m thankful for those rare moments where the red flags fly so high you’d think you were back in the glory days of Soviet Russia (where engagement break you!).

I end up with women that are wrong for me, which I suppose is true for anybody that’s not engaged or married. In hindsight, I can look back and say that these are not severely broken or undateable women. For all their faults, I can match them; for every piece of baggage, I carry my own. The simple fact of the matter is they were not compatible or healthy for me to be with on a long-term basis, leading to awkward interactions, uncertain motivations and broken hearts. And in every instance, I can always look back and recognize that there were warning signs from the beginning that I should have heeded, and in many cases they were mistakes and oversights similar to the ones I’d made before.

Problem is, I’m a sucker for a pretty face and expressive eyes. So when a woman does or says something so disarming to me it creates a pregnant pause in the conversation, I should just get up, put my money on the table for dinner, give them a kiss on the cheek and whisper “thank you so much” before walking away. Instead, I break the silence by taking their hand and saying “so what do you want to do on Saturday?”

One of these days, I’ll learn. Until then, I’ll keep making the dumb mistakes and hope history doesn’t repeat itself. If only Napoleon had been so tenacious, he could’ve made one Hell of a comeback at Waterloo.


So what about you, readers? What’s your favorite Red Flag story?

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22 Responses to Dating Week: Red Flags

  1. Gman says:

    A very intelligent girl with big brown eyes said to me, “Basically, I hate men.” We got married. We got divorced 4 years later.

  2. GenWar says:

    “Another example: you go out to dinner and the person you’re with gets tipsy before your food hits the table. Major red flag.”

    Hmm…I guess ‘red flags’ are situational/contextual/personal as well. `Cause, right there, I’d say you found a winner ;)


  3. Casey says:

    How about this comment, “I’ve cheated on every woman that I have ever been with, until you of course…”

    But when you are both young AND stupid, you find that comment flattering. Now, a few years older and much wiser that relationship is of course over, and I pay very close to any statement that includes, “Until you…”

  4. Chuck Miller says:

    This happened to me around 1991, a few years before I met my wife. I met this girl at a bar, we hit up a great conversation, we went out on a couple of dates, she was fun and vibrant and smoky hot. After our second date, she asked if I would like to come over to her apartment. She wanted to tell me something, and she thought back at her place would be a nice private location.

    This was great. I could not believe my luck.

    We went back to her place. She invited me in and asked if I would sit down on the couch while she went into her bedroom for a moment.

    In the back of my mind, my 70’s R&B playlist was queueing up. Teddy Pendergrass. Barry White. Marvin Gaye.

    She came out of the bedroom – carrying baskets of skin conditioner and moisturizers. “Have you ever wanted to make your own money?” she asked me.

    Not sure where this was going, I replied in the affirmative.

    “See, I wanted to talk to you about being one of my distributors for Nu-Skin skin care products.” She suddenly went, in the span of about 30 seconds, from bow-chica-wow-wow to oh my Lord she’s involved in a multi-level marketing pyramid scheme.

    “Um… I think I have to leave.”

    “What’s the matter, Chuck, don’t you like money? Wouldn’t you want to make enough to retire at 30?”

    I grabbed my coat. “I had a great time this evening. I hope you did too. But I gotta get up early for work tomorrow. Gotta go. Bye.”

    As I closed her apartment door behind me, I could hear her saying to me, “You just wait, one day I’ll drive up to your house in a brand new Cadillac.”

    Surprisingly – and thankfully – 20 years later, that Cadillac hasn’t arrived at my address.

  5. Cute~Ella says:

    HAHAHA I love that you bring Napoleon into dating blog posts.

    My favorite red flag wasn’t a dating story, but a friendship story. I ended up getting burned pretty bad by someone I knew for years when they decided that everything wrong in their life was my fault and I was a terrible person for not supporting them more. I should have seen the signs long ago and realized they didn’t want a friend, they wanted an enabler.

    As for dating, I see too many red flags and bounce as soon as they show up…sometimes too soon.

  6. Jennifer says:

    That sucks but reading that I almost want to say, that poor girl. Not because she was left…s**t happens…but because three years after the fact she is still so deeply troubled by it. Girl needs therapy. How masochistic to carry that picture around.

    But on topic, yeah, red flags. That feeling in your tummy, that voice in side your head. Hindsight being 20/20 had I heeded my red flags I would never have gotten married and thus divorced two years later.

  7. Cute~Ella says:

    RE: comment #2

    I’d like to note that I’m pretty sure that’s why @genwar adores me…

    Which could be another Red Flag story in itself. RED FLAGS OF AWESOME that is. :)

  8. derryX says:

    I gotta remember to be conscious to not raise a specific red flag. I actually was on a date last night; I found myself biting my tongue a lot when talking about past experiences, because I was about to say “we…”

    Remembering that the experience was shared with my former partner was not the important part of the story; the important part of the story was that I experienced it, and luckily I was able to catch myself most of the time. That being said, it did slip a couple of times, but I think the young lady I was sharing company with understands (she is actually fully aware of my situation, so I’m sure she understands). But, I have to remember in case the next person is not fully aware; not that I don’t want to be open about it, but because I don’t want it to be a red flag…

  9. GenWar says:

    RE: Comment #8

    I don’t think it’s about the flags, themselves, DerryX. I think it’s what they are indicative of. You can’t stop being yourself with your experiences, even if they involved a previous partner. But, if you are ready to move on, simply referring to those experiences (and that partner) is not a red flag, in and of itself. In the OP, the poor example girl was not letting go and thus, not ready to move on…that was the REAL problem. (#justsayin’)

  10. derryX says:

    @genWar I totally understand the difference. I just wanted to share my real-world perspective about not wanting my nuance to become a red flag. #justsayin’

  11. Amanda Talar says:

    We were out to dinner…his phone rang. He ignored it. It rang again, and again. I said “Do you think you should take that?” and he said “OK…yeah, probably” He excused himself from the table. He came back, white as a ghost and I said “Are you OK? Is everything OK?” and he said he had to leave because his ex-girlfriend was about to deliver their first child. There was no second date.


  12. Ski says:

    Is it sad that I was laughing through this whole thing? I’m so sorry, Kevin. But I’m also sorry for that girl.

    Red Flags are so tricky. I’m all for airing a bit of baggage, early on. People should know what they’re signing up for, to a point. But once, honey. Just once and they get the hint.

    My red flag: Talking overly sexual as soon as the girl shows some interest. Seriously, guys. You aren’t being clever and it isn’t flattering. In fact, it’s kind of icky.

  13. Gman (#1) – I’m pretty sure I dated her as well. Not literally, but you know.

    Chuck (#4) – That is a FANTASTIC story.

    Amanda (#11) – “There was no second date.” For you or the ex in labor? ;)

  14. Darcy says:

    When women try to make you feel guilty for being inattentive before you’ve met for your first date or even expressed any kind of formal interest. Red Flag.

  15. bklyn says:

    As GMAN has already learned…I have also learned to take what people tell you at the beginning of a relationship seriously. I had a friend’s date tell her he was used to getting his own way, always. She knows now to listen.

  16. I feel so sorry for the girl you went on the date with. Without some good therapy, that is going to haunt her for the rest of her life. It will also ruin every date she goes on. That is so very sad.

    As for you, Kevin, did you ever consider writing a book about dating? These are quite the wild/crazy/scary stories you have. I think you could definitely sell a few copies. Just sayin…

  17. Ellie says:

    A really shitty therapist said to me once upon a mentally manic time that we all wear masks to hide our flaws in the first few months of dating. We hide anything that could be unattractive; we don’t fart.

    My red flag of late? Guys who do these little things that just assume I am somehow their’s in a personal relationship – peeing without the door shut, assuming he must no longer do nice little things to woo me, and most importantly making decisions about our lives as if we are married.

  18. Laurel says:

    I’ve had several guys actually yell at me on dates for being taller than they are. Not only am I not inordinately tall, I’d met each one in person, so it wasn’t like my height was a shocker. If a guy rages out over something like genetics, I assume there’s a lot of other things he can’t handle. Dealbreaker!

  19. Noficazal says:

    For me the only red flag I would see at this time would be attempts to move too quickly to carnal relations. Translating to, “I don’t really want a relationship, just said activities.”

    The biggest red flags I raise are complete lack of any relationship experience at 27 and a nearly unhidable loneliness that leads to a bleak outlook on existance until it can be quelled.

    I assume that my best friend sitting nearby me is not a flag at all, but rather perfectly normal. Said friend is a yellow electric mouse with a lightening shaped tail, two brown stripes on his back, pointed brown tipped ears, and two red electric pads on his face. Sorry had to add a little humor and I forgot the one I was originally going to add.

  20. I was a walking/talking red flag in my dating days . . . wrote a piece about that for Metroland nearly a decade ago, archived for posterity’s and embarrassment’s sake here:

  21. kriskaten says:

    wow, #5, still?
    there are two sides to every story i suppose…
    i am awesome at ignoring red flags till they bite me in the ass. i’m getting better – now when a guy tells me about their arrest and parole record on the first date, i bolt. on the second? depends on how cute he is. sigh.

  22. Lauren says:

    Date number two was driving to Walmart parking lot to pick him up, because he got stopped by police on the way to pick me up for driving drunk.
    How did he not get a DUI? WTF?

    The policeman asked him not to drive and to find a ride home…it was THEN that he told me he’s been in and out of rehab/AA…you name it!

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