A Year of Living Flirtatiously

A commenter writes in to tell me I'm wasting my time with younger dudes--that the vast majority of them will not give me the kind of long-term relationship I'm after. (Which begs the question: What kind of relaitonship am I after?) Peeps: What do you think? Is it  all right to date one or two younger men, tops, but should a lady of 30+ years move on after that? Or should I be looking for a connection, the age thing be damned? Or am I gonna end up 40, 45, 50-- lonely and miserable--with that kind of attitude?

Being too eager to win anyone's approval is a big turn-off. Dating coach John Keegan has pointers on how you can avoid falling into the approval trap--and how you can turn things around, so that you're the powerful one who is bestowing (or withholding) approval.

I'm going to make Hot Band Guy fill out a post-date questionnaire that I'll let all of you read. Soo ... what shall we ask him? What do you want to know about the dating patterns of hot band guys? And what do you want him to tell you about me?

Two different guys asked me out for second dates over the weekend, and I refused them--only to be chastised by Arlo (once again) (in private rather than on than on my blog, this time) for not giving people a fair shot. ... Which has gotten me thinking: Am I too picky when it comes to nice guys--and not picky enough when it comes to getting hung up on players like Baby Fireman? Why do I turn down nearly every dude who asks me out for a second date? Do I automatically discount anyone who seems too into me? And should I resolve to give everyone who asks me a second date from now on?

The dude who runs "Nerd Nite Speed-Dating" gives us some insights on how to win over hot geeks.

A musician I've flirted with recently blogs about me blogging about him! And then emails me to tell me about it. Ooops!

Last night, I lost my speed-dating virginity ... at Nerd Nite. (Don't laugh. Nerdiness ages well!)

The New York Times recently ran an article that indicated that texting is helping to erode the fabric of society. Is technology improving our sex lives while destroying our chances for meaningful relationships and long-term happiness?

In the (darkly funny) movie HAPPINESS, two characters are out on their first date when the woman tells the dude about how she killed her doorman. I'm going to go out on a limb here and say that's better left to the SECOND date. ... What other topics should you skip till you get to know each other better?

The owner of FLIRT (one of my favorite stores here in Brooklyn) shares her insights on how to dress with a little attention-getting flair.

I invite a dude to hang out with me and my friends ... and after getting his response, I have to wonder if negative-thinking might help toughen me up and make living flirtatiously easier.

You guys remember Mr. Tweed Jeans--he of the extended flirtation at a party two weekends ago? He who, despite seeming to be quite interested and talking to me for, like, 30 minutes, didn't get my number when I said I was taking off? Yeah, well, I invited him to hang with me and some friends ... and ... 

A new site has the funniest e-cards I've ever come across. There's one you can send to an office crush, one you can send to that great guy you just went on a first date with ... and a couple that would be appropriately inappropriate for the dude you're shagging. Which ones are your favorites? (Fair warning: Some of them are a little dirty.)

I did everything wrong on Saturday night, when trying to pick up a painter from Portland, Oregon--including telling him about some of the other romantic entanglements in my life. Can you guess how this debacle turned out?

Please don't try any of the maneuvers I pulled on Saturday night. Today, I'll tell you about the first three of them ... and tomorrow, I'll finish off my Halloween saga.

Or do we have to be ready before we can find it? I sort of feel like I could love Barnaby Jepperdoom--maybe--if I let myself. (Let's keep that between you and me, shall we?) But do I still have commitment-phobia? Or is it more that when you find the person who is REALLy right, you don't have to talk yourself into getting serious--it just happens?

Am I being kind of pathetic at this point? ... Also, I still don't have a Halloween costume, despite the fact that I had 5 sexy possibilities lined up last week. What should I be? What are you guys gonna be?

Sort of--according to a recent study. But you have to play in a very specific way.

Saturday night party. The cutest dude in the room asks me what I do, and I say: "Why don't you guess?" Then we talk for a good thirty minutes ... but ...

When we meet someone new, we always want to know his (or her) name, job and hometown. And yet asking those questions can make you come off like a boor--like you're conducting a job interview instead of really getting to know someone. Dating coach John Keegan comes to the rescue! Ask the Big Three Q's according to his suggestions and a person will feel intrigued, not interrogated.