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Simply Solo Spotlight: Lessons from a Serial Dater

May 3, 2011

It’s Simply Solo Spotlight Tuesday, and I’m pleased to introduce today’s guest blogger, Kat from After I Quit My Day Job. I first read Kat’s blog when she was Freshly Pressed last summer – as she began her journey to go on 30 dates in three months. Kat is an amazing writer, and it’s incredibly fun to live vicariously through her very busy dating schedule. I don’t know if I even have enough outfits to keep up with Kat’s dating itinerary (and she has awesome outfits, which she often details on the blog with pictures!). After enjoying this post, be sure to stop by her blog.

Quick shameless plug: Do you have a story to tell? Advice to offer? Did you just have literally the worst date of your life and you must write about it? I’d love to have you as the next Simply Solo Spotlight! Contact me at:

Lessons from a Serial Dater

Photo courtesy of "After I Quit My Day Job"

To say that you’re good at dating is like saying you’re good at losing weight: if you were as good as you claim to be, you wouldn’t be stuck still doing it in the first place! Nonetheless, I am—for better or worse—guilty as charged. Although I have yet to transcend the annals of for an actual relationship, I’ve been on 26 first dates since August and seeing as most of these first dates have resulted in the request for a second, I thought I’d compile a few of lessons I’ve learned along the way.

Let’s get the boring bits out of the way, shall we? If you decide to try your hand at the whole online dating thing, you need to play it safe. Ask your potential soul mate for his name (his full name) before you agree to meet up and once you have his details, Google his fine self!

Stalking is more than permissible when it comes to or eHarmony but once you’ve established that he’s not a serial killer, you may want to cease and desist. (I gave myself a total inferiority complex when I realized one of my dates was a blue blood, Ivy-educated psychiatrist from Philadelphia’s affluent Main Line.)

Next, you’ll want to establish a meeting point and this meeting point should be somewhere public (ie. not a candlelit dinner for two at his serial killer compound). Then, once you’ve agreed on the where and when, you should provide a close friend or roommate with this information (and an approximate time by which you expect to return), just in case. Make sure you have enough cash for an emergency cab fare and the number of a reputable taxi service programmed into your cell phone.  

Now, let’s move onto the fun part!

In my opinion, getting ready for a date is half the fun. I’m always dying to try a new outfit or a new hairstyle but take my advice on this one: unless you’re unemployed and have hours to sit around getting ready for a date (and recovering from whatever fashion faux pas you’ve inadvertently committed), this is no time to get creative.

Stick to a look that you know will work.

And even if you do have tons of spare time to spend on primping, don’t. If I’ve learned anything from my Great Date Experiment it’s that the amount of time spent getting ready for a date is inversely proportional to the amount of enjoyment you’ll actually experience on said date. In other words, the more time you spend getting ready, the more your expectations are going to build and the greater likelihood that you’ll be disappointed. It’s better to go in with low expectations and be pleasantly surprised than to discover your potential soul mate has shown up in jeans and a t-shirt when you’ve just blown your entire paycheck on a new outfit. Not that I would know anything about that…

Concentrate on basic hygiene (clean fingernails, fresh breath, etc.) and remember: when it comes to makeup, less really is more. If you go all out on a first date, you’ll have to spend the rest of your relationship keeping up appearances. It’s better to go for a more natural look in the beginning. This way, if you end up going on a second date, you’ll know he’s interested in a repeat performance because of your brains and your beauty and not just the amazing smoky eyes you’ve managed to create with your jewel-toned eye shadow.

Once you make it to the second or third round, you can whip out your five-inch stilettos and really dazzle him but unless you plan on being perfectly made up at all times (even, for example, when you’re in bed together) you want him to be pleasantly surprised (sound familiar?) when you make an effort to look stunning, not disappointed when you don’t.

Now that we’ve covered date set up and date prep, it’s time to move onto the actual date itself.

Be prompt, be polite and, even though this is easier said than done, be yourself. If you’re naturally a bit goofy, don’t be afraid to show it and if sarcasm’s your thing, now’s the time to see if your date can handle it.

Like most women, I tend to project. In fact, I’m worse than most in that I project from both sides of the equation: I project past boyfriends onto the current contender (Will his mother hate me? Will he cheat on me?), and, as if that’s not bad enough, I also project the current contender into the future.

I wonder where we’ll get married, where we’ll honeymoon and where we’ll live, all before I’ve even decided if I like the guy.

So come prepared with a few funny stories to share, don’t take yourself (or him) too seriously and avoid saying things like “We’d make beautiful babies” or “Your place or mine?” (If you’re hoping to develop this date into an actual relationship, sex on a first date is an absolute no-no.)

Let him open doors for you, let him make recommendations on the menu (if you’re into that sort of thing) and let him pay. I always offer to take care of the tip on a first date and even though I never expect to pay for my half of the bill, I make sure that I have the means to do so, just in case.

As for kissing—well, surely you don’t need me to tell you what to do there! I promised myself I wouldn’t kiss anyone on a first date when I began my Great Date Experiment back in August but that little resolution lasted all of a week and a half.

Listen to your gut (as long as your gut doesn’t say “Take him home and shag him.”)

The follow up “Thanks for a lovely evening” text is a nice touch (especially if he’s the one to send it). If you can work in some sort of flirtatious yet subtle hint that you’d like to see him again, all the better, and if you manage to include a new inside joke in your communiqué (thereby confirming your rapport with one another), you’re golden.

I’m afraid that this is where my expertise ends, although I suspect that this is because subconsciously I do my best to keep it this way. I love the thrill of meeting someone new, of selecting an outfit and slipping into my stilettos for a drink at someplace I’ve never been before and the possibility of a first kiss.

Nonetheless, I know (or at least I hope!) that someday I’ll meet a man with whom I really click— a man I’ll like even more than I like dating— but until that day comes, I’m going to go right on enjoying myself as I perfect my technique and I suggest that the single amongst you do the same!

12 Comments leave one →
  1. May 3, 2011 8:46 am

    Great dating advice.

  2. May 3, 2011 9:43 am

    Nicely written and wise advice!

  3. May 3, 2011 11:04 am

    Thanks for the dating advice, and saying it’s OK to date a little or a lot. I’m learning as I go…

  4. Zak permalink
    May 3, 2011 11:06 am

    I am all for a woman being herself on a first date – and would offer that same advice to guys I know – since I don’t want go out with someone three or four times – if I’m that lucky – only to find out they aren’t as awesome as I hoped they’d be. Also, goofy goes over really well in my book, and lack of goofiness might not get someone a second date. Just sayin’…

  5. May 3, 2011 11:15 am

    Thanks for a great guest post, Kat!

    “Next, you’ll want to establish a meeting point and this meeting point should be somewhere public (ie. not a candlelit dinner for two at his serial killer compound).”

    You literally made my laugh out loud with this. I’m totally a worst-case-scenario kind of girl and these kinds of thoughts always run through my mind. Dating is dangerous!! 🙂

    “I wonder where we’ll get married, where we’ll honeymoon and where we’ll live, all before I’ve even decided if I like the guy.

    Umm. Guilty. It reminds of “He’s Just Not That Into You” when Gigi realizes that some guy likes her, and her friend immediately says, “Let’s plan your destination wedding.” Seriously? Why as girls do we do this!?? Why do we spend so much time thinking about future plans with a guy before taking the time to figure out exactly what we think of them? OH! And don’t get me started on this – why do we also worry soooo much what they think of us – will they call, do they think we’re pretty, do they think we’re smart – before saying, wait a second – I don’t even like them that much!

    We’ve got to stop these sorts of thoughts/behaviors if we’re ever going to be on an even playing field when it comes to dating.

    (Sorry, you got me all riled up. Maybe it’s also because I drank some iced coffee this morning and I never drink coffee.)

    • May 3, 2011 12:26 pm

      Thanks for the lovely intro Catherine, now lay off the iced coffee! 🙂 But you’re right- I know very few men who obsess over thing as frequently (and as EARLY into a relationship) as we women do, and those I DO know scare the living bajeezus out of me, especially after the debacle with the Bovary Reading Bachelor…

      The one good thing about serial dating (okay, there are actually a lot of good things about serial dating but I digress…) is that you get to a point where you lose the mental energy to get all hyped up over every single guy you meet. I mean how many different weddings can a girl mentally plan? Lol!!!

  6. May 3, 2011 11:38 am

    Great tips, Kat! I always enjoy your posts.

  7. May 3, 2011 6:48 pm

    This is great! I need these tips, as I am recently single, and waiting to start dating again. I love the part about not spending too much time getting ready. I absolutely agree. It’s like you jinx the date if you primp for hours. Will definitely start following Kat’s blog now.

    happy dating!

  8. May 3, 2011 11:09 pm

    Remember that your date wants a general idea of your title and job description. If youve recently graduated form school you might want to talk a little about that.

  9. May 5, 2011 5:01 pm

    Do serial killers have compounds?
    Well, I guess if their names are Osama, we know the answer to that one!

    Great advice, thanks for sharing.

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