-or- “Terrible Flirt, Terrible at Flirting”

Our second installment for Dating Week is based on the same conversation with the two men we will refer to as Adam and Paul, because those are their real names.

As the evening wore on, Adam, Paul and I continued to bond over tales of what it was like being 28 and single. As was touched upon yesterday, we discussed the folly of trying to pick up a potential mate in bars and how we still try anyway.

According to Google Image Search, this is flirting. Here, a happy young man employs one of my favorite flirting tactics, what I call The "In Comes the Airplane Neeeeeoooow" Maneuver.

Talk then turned to the last time we found ourselves at that same establishment. It was the same large group of people: a mixture of gay and straight folk who pursued theatrics as a profession or obsessive hobby. Oddly, we also ended up in almost the same exact area of Oh Bar on Lark Street, except the seating arrangement was different.

The last time we were there, I sat next to a girl with whom I’d struck up some swell conversation earlier in the evening. Through a friend of a friend of a friend, I was brought in to perform in a staged reading that she was also cast in. We ended up sitting next to each other. Since I didn’t know anyone there, I got down to the business of getting to know her. Also, she had these incredible eyes.

For the sake of maintaining anonymity and not embarrassing myself fully, we’ll refer to her as Redacted.  Would you believe that’s her real name? Good, because it’s not.

After the performance, we ended up being dragged to Oh Bar. My friends and I talked about a lot of things, including my passive interest in her. We ended up, just as in the performance, sitting next to each other. Not by design, but rather because of the placement of people we knew and with whom we were most comfortable. I had intended to make a play by striking up some more playful conversation with Redacted, and talked to a couple people about her unusually striking eyes. Unfortunately, I ended up getting shut down.

“No, you totally chickened out with Redacted,” Paul interjected.

Wait, that’s not—-okay, yeah.

I swear, I was within seconds of telling Redacted what fantastic eyes she had, but then she gathered her stuff and was saying her goodbyes. Okay, not within seconds, but I was about ninety percent towards working up the courage to tell her. And with such a large group and not enough chance to transition towards the compliments and flirting, I thought it’d be awkward to say “hey, it was great meeting you and you have fantastic eyes, can I have your number?”

…okay, I chickened out. I would have worked up the courage, though, honest! Well, most likely I would have. Maybe.

But probably not.

Some of my friends have said I’m a terrible flirt when it comes to women, but not enough to have me convinced that’s actually the case. If anything, despite my occasional prowess, I’m terrible at flirting.

Sure, it’s really easy for me to flirt when there’s no pressure to do so. If I just happen upon a person and strike up a conversation and/or if I know the exchange won’t lead to anything (because they’re not available or interested), I’m golden. Put me in a social situation where I’m just being casual and need to entertain multiple people throughout the course of an evening, and I’m Cary freaking Grant.

When it comes to someone that I actually meet or see and then get interested in, however, I’m the furthest thing from Cary Grant (Skeet Ulrich?). I find trouble locating a common ground for conversation, distract myself with the people around me, and ultimately end up driving her away with what appears to be a shy aloofness but is actually just brazen incompetence.

Now, this isn’t always the case. Sometimes, in fact, I’m pretty good. The mood will strike me, I’ll get my confidence at just the right time, and I’ll be able to…well, maybe not charm the girl, per se, but at least keep up my end of the conversation. For the most part, though, I find myself in a true quagmire: when I try to flirt, I fail. When I don’t intend on pursuing anything, I end up being a super flirt.

The solution: I have to make a conscious effort not to flirt, so that I can flirt.

Oh my God, I’m going to die alone.


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21 Responses to Dating Week: When it Comes to Flirting, I’m a Charming Coward

  1. Jennifer says:

    Your last line says it all (not the one about dying alone!) “I have to make a conscious effort not to flirt, so that I can flirt.” Don’t put so much pressure on yourself to be funny and charming and complimentary and just let it flow. If the conversation is good and you’re clicking, forget the amazing eyes baloney (I’m sure it’s true but 1. she’s probably heard it before and 2. it makes some people feel awkward when that stuff comes out of nowhere) and just tell her you’d love to hang out sometime. If she’s on the same page numbers will be exchanged and you can go from there.

  2. Erin Morelli says:

    I don’t necessarily consider myself to be a “bad flirt” since playful banter seems to come pretty naturally with me. My issue is usually that of crossing the line from banter to the next step. Some times this might be getting a phone number, other times this might be asking for a formal date. Being female, I always feel awkward making that kind of move since it’s stereotypically the male’s role, but I know with women empowerment and all that it’s more socially acceptable now, I just have this fear of being rejected face-to-face. So sometimes I will resort to email/IM, etc, to be more bold, but then have the issue of being impersonal. Socializing can be so confusing >.<

  3. Cute~Ella says:

    I’ve seen you in action and you’re not too bad at it. ;)

    But I see a lot of myself in your flirting, when nothing’s on the line? We’re pros! If something’s on the line? Well we’re not so good at it…but one day a while back I just decided that nothing was ever on the line. They’ll either like me or not and if the answer was not? Hell, we live in the ALB area, potential dates are like buses, if you wait 20 min there will be another one along…if you want to take it that is.

  4. Ski says:

    What the hell is flirting? I find nothing sexier than a guy who is confident in conversation and actively listens to me, like I’m the only one in the room. (Even if we’re in a crowded bar or with a big group of friends) As soon as some one uses a line on me, it pretty much ruins every thing. I’m put on the spot. Do I respond in kind? Where do we go from here, conversation wise? Keep talking about my eyes?

    The most successful guys for me have been, 1. Conversation. 2. Buy you a drink to continue conversation? 3. Let’s exchange numbers to keep talking.

  5. Karl says:

    Is it because it’s stereotypically the male role, or could you be using that as an excuse? No offense. But I’m a great offender as well. After a long night of not-hitting on the person I’m interested in, I can come up with a laundry list of reasons why I didn’t seal the deal, but in the end, I know- it’s just ‘cuz I was chickensh*t.

    imho: it’s the fear of rejection stemming from a lack of confidence somewhere. so focus on the things you are confident about and try to ignore your flaws. also get rejected a few times, after awhile, it’s not so bad anymore, lol. I’m being totally serious; works like a charm.


  6. Jessica R says:

    I think that I am pretty good at carrying on a conversation with a guy I’m interested in, but a male friend recently told me that I need to flirt more. Trouble is, I used to move into relationships too fast, and that caused trouble for me. Now I vowed to move into relationships slower, but this means I try not to me very phsyical on the first few dates, or to be “all over a guy” if we’re at a bar, or such. I don’t want to give him the impression that I want to jump into bed with him right away (even if I kinda do). The downside is that I think several guys I’ve dated casually just figure I’m not that interested in them, even if I am. I tried to counteract that by verbally telling them I had a good time, or want to get to know them more, but it doesn’t seem to be working.

    So, I guess I want to know, from a guy’s perspective, what amount of physical flirting will get my point across, but not make it seem like I’m easy.

  7. #5 (Karl) – Normally I’d agree with you, and to an extent I did chicken out. But honestly? It’s not that.

    Rejection’s not an issue for me. It used to be – in a big way – but now hearing the word “no” or getting a cold shoulder gets brushed off like so much dirt on Jay-Z’s shoulder.

  8. I say just be yourself and if it is meant to be it will happen. It sounds like you are putting way too much pressure on yourself. Just engage her in conversation and let if flow.

  9. Amanda Talar says:

    Such an honest post!

    Maybe Miss Fantastic Eyes will see it? :)

  10. Gman says:

    I have only two pieces of advice:

    1. Never introduce yourself as Neville Chamberlain.

    2. Introducing yourself as “Chester Alan Arthur, but you can call me Chet” works, because she’ll either get the joke and you will both be at immediate ease, or she is a doofus and you won’t care what else you say all night.

  11. James Frederick says:

    Jessica, what do you mean by “it doesn’t seem to be working?” Do you mean you aren’t getting calls for second dates? How about saying, “when do I get to see you again?” or giving a kiss on the cheek? That would keep me interested without thinking that we are just going to “jump in bed” the next time.

    And serioulsy, Jessica, ask a dude you like for his number if you just met him — for instance, at a bar. Maybe he is thinking, “oh, she’s leaving… she said she had a good time talking, but she is actually leaving, so she was probably just being nice.”

    A shy, somewhat uncertain, “can I call you some time?” will have me wrapped around your finger!

  12. Steve says:

    What you need to do is steal her purse. That way you can be like “Oh, I seem to have stolen your purse. How careless of me. Why don’t you give me your address so I can return it and we shall laugh about it over drinks.” And then, during the afore-mentioned drinks, maaaaybe a certain diamond ring is slipped into her chianti? Oh my, how did THAT get in there? ;)

    PS: YOU put the diamond ring in there.

  13. Amanda Talar says:

    Steve, you give diamond rings away on a first date?!

    What’re you doing later?

  14. OK Two things…

    #8 (Michael) said the same thing I’ve mentioned in the past. :)

    Jess, find out who #11 is, and get some dinner!

    Finally, if I had been there, I could have done the, “you know my friend over there…” just like in 7th grade.

    I too am the biggest chicken when it comes to the “dating” game, which is why I choose NOT to be single. I have no idea how I’d manage if I were single again. I’d probably join you in the “I’m going to die alone” party!

  15. Steve says:

    Why, are you a cop? Follow-up question: Can’t you see that I love you?

    And there you have it! Kevin Marshall in the Present Tense has created its first love connection!

  16. Jenifer says:

    Love this post! I want to read more. Kevin, you are very charming and witty and a great listener. Those are fantastic assets for business or romance, so focus on those, and just be yourself!

    I agree with #4 that the best pick-up is having a great conversation with someone, covering anything of common interest, from pop culture, to world events, to your personal story (where’d you grow up, that sort of thing). Once you discover what makes them tick you can be more creative and personalize your approach (i.e. she loves Mexican food, so invite her over for taco night!).

    When I got together with my current boyfriend (of almost two years) he took me to a pet shop so we could pick out a birthday gift for his friend’s 4 year old son (he bought him a hermit crab, by the way). I thought it was the sweetest thing! And countless other times he has said or done something based on some small observation of something I liked or wanted to try. Expressing interest in someone else and their interests is usually all it takes to figure out whether their interest is mutual. And, like #3 said, if they’re not, then move on to the next object of your affection.

    P.S. I believe that true love is out there for everyone, and you will find it so long as you keep looking.

    P.P.S. And keep writing… smart guys are sexy!

  17. Ellie says:

    That Kevin Marshall – he’s a modest guy. Calling himself a sex symbol, I mean really, that’s just so humble! (I keed, I keed. With lurve.)

    Having known you for years, I can say that you are good at flirting.

    My own problem is that I need to be hit with a frying pan or something when it comes to men. I’m oblivious to come-on’s. So only the crazy ones, the ones with the outlandish behavior, gets my attention. The nice guy who is just dancing near me? I don’t notice it because I’m so caught up in feeling awkward. The crazy guy who tries to monopolize my time? Well, I notice that…

    So I think my thing is that I’m probably not the only woman who is clueless about subtle reactions. Maybe the girl is waiting for that obvious sign you like her and when she’s not sure she’s getting it, she leaves.

  18. Jen83004 says:

    Completely agree with you Kevin, as have other readers. When nothing’s on the line, we flirt like pro’s, but then when we think the other person could be a potential mate, we freeze up. I’ve so been there!

    Keep writing–I enjoy reading your blog from a guy’s perspective.

  19. James Frederick says:

    Ellie, I so want to agree with you. That the girl is waiting for the obvious sign from the guy. But, there is a fine line for a guy between giving an obvious sign and being a creep… especially on a first meeting.

  20. Ellie says:

    James, totally agreed. There is a fine fine line between being gallant and being a creeper. Maybe I really am Albany’s Liz Lemon; it’s not out of the realm of possibilities.

    Case in point: Last month I was out dancing. A very handsome and charming guy was dancing in such a way that he wanted to dance with me and probably get to know me better. I needed a glass of water and ranted to my friend that no guy was even looking at me and I’m a relatively attractive gal. She bopped me on the side of the head and pointed out the guy who had been trying to get my attention all night. I hadn’t noticed him because he was being subtle. We ended up having a nice conversation, but it led to nothing. And through no fault of either of us – he was called with a family emergency and fled to handle it.

    On the other hand, I did notice two guys who were also attracted to me that same night. And they were the creepy kinds.

    I have given up on even trying.

  21. Noficazal says:


    I read this post initially on Tuesday and wanted to comment then, but wanted to think on it a shade first. I have a penchant for making comments too long, but will try to keep it short.

    First off, you mentioned at the end that you are going to die alone. I am 27 years old, have never been on a date, or even gone as far as kissing another. I am outstandingly shy in the majority of situations and since I am a guy and expected to approach others, this seals my fate. If you have any data that you have achieved more in the realm of relationships, I call to question the “die alone” claim on your behalf, though I know it was posed in a joking manner.

    I have the basic mindset that any lady being nice and staying around me for any amount of time is either being nice, having fun, acting as though they feel they are socially obligated to, or trying to see how I would react to such subtle overtures as a joke. I have thus blinded myself to all but the most obvious of signs. If a lady that I was at all attracted to said that they thought they might like more or would like me to see me sometime, I would not hesitate unless fairly obvious signs of malice intent were seen. Perhaps this is because I cannot imagine a lady truly being interested in one such as I, though I have no good reason for this stance.

    In regards to some of the previous comments, I would probably be very slow moving forward without an external push. If theoretically I had been out a time or two with a lady and she just said that she was interested, I would completely believe her. Conversely, if early on measures were taken that seemed intent on carnal activities, I would more likely shy away because then it would seem as though she were just looking for “fun” and not something more meaningful. I have a propensity to fall easily, so such an arrangement would more like than not be detrimental to me.

    Also, I have a strong desire to be “good” and not fall to the trappings that many guys I have seen have fallen to. I am overly respectful and actually get upset with guys when they talk or ladies in a disrespectful or objectified manner. Due to this, I find it easier to talk to and be around ladies than guys, but my position in such situations seems to be closer to brother or eunuch than anything else. Which is fine as long as others don’t feel uncomfortable with me around and I can possibly bring some light or happiness to their existence.

    To conclude, I am too shy to approach anyone, I don’t know if it is a hidden fear of rejection or what I see it as, a desire not to make the lady feel uncomfortable or in any way induce negativity through my intentional actions. As such, I have mostly resigned myself to my fate of forever being alone. If you have a plausible way to prevent this that even one such as I can do, feel free to let me know. Either way I will try to keep helping others and doing what I can to make their existences better, if only for a moment, before to loneliness eventually finishes crushing me.

    (this is the reduced version, self edited for tangents, some unimportant content, and the ilk; nothing included herein is something I would not be willing to say to you or another in person; by the way, it you remember me you actually know me from a college in Loudonville that I graduated in 2005)

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