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Recent experiences have left me confident there is nothing left about dating and friendships in Boston to shock or surprise me.

Nonetheless.

In January 2004, my inaugural online-dating foray, via Craigslist (before it got completely weird, natch), resulted in a uniformly spectacular one-night stand with a fellow with whom -- by the nature of the one-night stand and how it materialized -- no further friendship or relationship or hooking-upship was desired or necessary.

A great learning experience (she says with a wink and smile).

Last night. Via OKC. A message:

"Hello my old friend... You look fantastic. Remember little old me?"

Him. He. Mr. Craiglist. Scooped from the memory banks and into new reality.

Unreal, I say. Unreal.

(I'm still working on the incredulous comeback.)

35 red x-marks

Everything I've learned about organization, I learned from the 1980 movie Nine to Five.

You know, the film where the three ladies from Consolidated take down their "sexist, egotistical, lying, hypocritical bigot" of a boss Franklin Hart (Dabney Coleman, natch!)....in part by harnessing him to a garage door opener in his bedroom until the invoices from Ajax warehouse arrive in the mail. (Four to six weeks, this takes back in 1980s office land.)

For dramatic purposes, Violet, DoraLee and Judy (l-to-r, above) keep track of how long they must incarcerate the odious Mr. Hart. So they create a wall-sized flip-chart calendar. During several musical montages, they mark off each day with a red "X", interspersed with various scenes of Consolidated's ever-improving atmosphere.....flowers placed on desks, daycare centers opening, punch-clock eliminated, company alcoholics going sober, orange paint going up in the locker room.

It seemed to work. In the end, Violet takes over the company and Mr. Hart gets sent to the jungles of Brazil, never to be heard from again.

I thought of that last night as I created the same for myself....to mark off each of the 35 days until marathon training begins on December 15. A calendar showing: what days I'm going to go to the gym, so I don't slack off. What exactly I'm going to eat each day, including a multivitamin. What time I'm going to make myself go to sleep (i.e., pre-midnight), no matter what juicy gossip is linked to politico.com or how much I want to play Scramble on Facebook.

After last week's string of 3 a.m. nod-offs and Reese Pieces binges (two), it was time to tame my inner Mr. Hart.

Faithful readers, I know this isn't as sexy as anonymous Craigslist chatting with casual dates. But there is an old trope about how it is easier to go on vacation when your house is in order. My house has been out of order for some time.

Wanna bet?

From Barbara Wallraff's Word Court, the "language question or dispute" column of The Atlantic (Sept. 2008):

DEL of Orlando, Fla.: "I am a retired librarian and occasionally, out of curiosity, look at Internet personals sites. It seems that most of the time people who want a discreet meeting say they want a discrete meeting. Webster's New World Dictionary, under discrete, does say in a note, '(see discreet),' but the definitions it gives--'separate and distinct'--are not what people are trying to communicate in their ads. Why the confusion in usage?"

WC: "Most visitors to personals sites aren't there to meet good spellers. Nonetheless...."

Speaking of open options....

Found in my e-mail inbox this morning from an address I didn't immediately recognize:

Hey ,

How are you ? How was the balance of your summer ? Whats new with you ?

D

And then it came back to me. Early July. My random Craigslist posting late one night about being lonely at home with my cats. Answered by this gentleman, producing racy banter that lasted several days before necessarily ending....primarily because I suspected he was married.

So he has held onto my e-mail address for three months and picked a random Wednesday in October to re-emerge?

So I ask, why don't the people I care about keep my e-mail address and ask how I'm doing from time to time?

Sheesh.

Done.

For a girl who hasn't dated in what feels like two presidential election cycles, last weekend was pretty darn social.

The aforementioned Organ Tuner incident Friday. A baby-shower BBQ for 25 for C&A on Saturday. The reemergence of a certain urologist from Indianapolis -- church friend last seen in 2003 -- that led to a Sunday lunch date and walk through the Public Garden.

I even attempted some valid networking later that night: drinks at Enormous Room via Opus Affair, a group that brings Boston artists together for a drinks outings. Risking egoism, I give myself points....I dressed up pretty, went by myself, knowing no one. Which proved to be a tough nut. The crowd stood in tight twos and threes deep in conversation; I downed one potent vodka drink, met one striking professional baritone, and left an hour later.

So, 9 p.m. Sunday instead found me over at M's apartment in Jamaica Plain. M is my girl gossip friend.....listening to months of ranting about Another Man solidified her credentials. In return she shares details of her own relationship (with a Republican!), itself full of aggravations. This summer, after six months of dating, M learned that her man saw this "relationship" much differently than she....as in, casual and not for the long-term. She's still deciding what to think about this but they're still together... which has produced months of fodder for our conversations.

In the meantime, I admire her: since they're only "casual," M has a side affair going on, just ramping up and very fresh. And which falls much closer in tone to my thing with the CFO. (Who, by the way, has been persona non grata for 13 days.) This is what we hashed out on Sunday, lounging on her bed in our socks, like a slumber party: lots and lots and lots about "casual dating," and what one should expect.

Speaking of the CFO, I left my conversation with M deciding I'm done with him. Done. Done. He ended his last message with a "talk soon." I've always believed that as a professional casual dater, if he wanted to end it, he would end it without a lot of fuss. But he has not tried to reach me, and he has not replied to an e-mail I wrote last Thursday.

However, he is continuing to post ads on Craigslist; joking with M, I bet that he was. So as we chatted I typed the words "playful" and "fit" (2 of his favorites) into the personals search engine. And sure enough, one titled "Sweetness" (another favorite) appeared from October 5. Using his writing style, language, overt exclamation points, neighborhood. Looking for playful, fit, ladies to keep warm with.

On the terms of our arrangement, this is certainly within his rights. Maybe I'm just jealous that he's driving for other dates and I haven't felt like it. Maybe I've lost patience with the arrangement. Or certainly expected that as casual as our arrangement was, he'd periodically check in before checking out entirely. M theorizes that he isn't cutting things off because he's trying to keep all options open. Well I'm hardly thrilled to simply be someone's open option....or maybe I was and maybe, again, I'm just done.

One of my favorite song lines ever comes courtesy of Semisonic, in "Closing Time": Every new beginning comes from some other beginning's end. Whenever something new starts I never want to think that it will end with me ultimately dissatisfied....yet in many cases, that is the case. There must be an end to be a new beginning.

Which is why I'm done.

Date #3e: The man's got energy....and ideas....

The CFO and I had a good time on Thursday night. This is no surprise. We have always had a good time together. On this evening it was at Audubon Circle, across the turnpike from Fenway Park. It's a decent slinky nightspot....I wore a short skirt and heels, he a sports coat. We sat at the bar and started with a couple martinis apiece, and the conversation picked up commensurate to the liquor infusion:

The Democrats and Obama. The shared anti-love of Sarah Palin. The AIG bailout and his panicked roommate. Parking tickets. The three dates he had been on since we had last gone out.

(Or, admittedly, the three dates he was telling me about. I don't doubt that there were more. This man knows how to work Craigslist like a fool. One date with a woman who had extra tickets to Tanglewood; another with homeplate seats to the Red Sox and looking for a date.)

He asked me about what he calls "my personal life."

I admitted that I've been on the low end of dating enthusiasm these days. Getting involved with the Obama campaign had switched up my focus, that match.com wasn't really floating my boat anymore. To his credit, he didn't say or do anything to make me feel inferior for that--other than, perhaps, having a half-dozen women to juggle other than me, which is one reason we hadn't seen each other since before Labor Day.

We moved down the street to a dive bar for a cap-off beer. We held hands across the table. The conversation got more personal.....his marriage and why and when it broke up. Why he likes going out with me. His offer to vet my match profile, since he thinks I'm a good date and should advertise it more.

I think if you asked me once what constitutes proper date talk, giving tips on how to best date other people would not have been high on the list. But again, it seems to be a popular topic with the CFO and me. And it doesn't seem out of place. I thought, and then told him, why not? Why not have the man who likes to date me help me tell other men about...me....

This was intense stuff and brought up some intense emotion. We ended up back at my apartment for our "satisfactory good night kiss," also intense. Which made me realize there is good reason we only go out once every three weeks. It's exhausting, especially for something so casual.

Date #3b: At long last, the CFO....again

I was reminded today that while it might be more fun to talk about hot men ogling my legs on Boylston Street, I owe y'all at least a cursory summary of my CFO date from last Wednesday.

You know, it went well, and no reason for the delay. In fact, I heard from the CFO late yesterday afternoon .....we almost made impromptu plans for last evening, had I not already planned dinner with some girlfriends. (Which, by the way folks, get over to Picco on Tremont Street for the eggplant/mushroom/ricotta pizza. Do.)

We are "pencilling something in" for the weekend.

To give you some sense of the situation: in an e-mail last weekend, he addressed me as "Sweetness." I replied that I was honored to be held in that esteem, along with Chicago Bears great Walter Payton. Yesterday, he began his message:

"Sweetness .. yes! You and Walter (nice company to be in, if you ask me!) Why wouldn't I think sweetness when I think of you? We've had two delightful dates now, both of which have ended with me smiling! You too, I hope!!!"

That's some serious exclamation-point action. He doesn't talk that way....I swear.

But it was a good time last Wednesday. A commonality we share is a love of working out.....so we met at 8:30, both coming straight from the gym. This left us with appetite for fajitas and sangria at a Mexican joint just down from my apartment, as well as for stories from the 3 weeks since we met at River Gods. All followed by another "satisfactory goodnight kiss."

Sorry to keep bringing up the liplocks, but they highlight another topic we plumbed verbally: my writing about him on this blog. He is all for it. (And approves of "CFO"; to his friends who know we have gone out, I'm known as "Southie.") We discussed how I characterized our first date in writing, particularly the (ahem) lengthy way we ended up saying goodbye.

Shall I say, if we continue to date, "satisfactory goodnight kiss" will become code for a great many things best left unsaid. Enough said.

The CFO is so far a gentleman who has been to town and back.....divorced, several long-term relationships, and a number of other women he's found interesting along the way. He's infused with joie de vivre.......flirting with the 69-year-old female owners of Ferraris until they give him a ride (a much longer story from the trip to California), rock climbing with his sons, effusively complimenting this much younger woman way more than he needs to.

We're aware of the 20 years of difference, and that I'm looking for a relationship and children and that he has no desire for either or more. But for the moment we hang out well and don't necessarily want to stop. We have strong chemistry. We've already shared piles of dirty laundry. We made a pact to always be frank....and because of the frankly casual nature of the experience thus far, it's been easier to be frank because there feels to be less at stake.

And did I mention that he strongly resembles Sean Connery?

Eat that, Matt Damon look-alike leg-ogler...! And my mother should be so proud.

Date #3a: It's all good

To ease the minds of all who might need easing, I survived my first Craigslist date and am not, yet, a casualty.

My 54-year-old correspondent turns out to be the Chief Financial Officer for a non-profit in Newton. Tan, bald, white beard, really did bike 40 miles in the White Mountains over the weekend, happy to see me. We met Tuesday night at a bar in Cambridgeport I've always wanted to visit.....River Gods on River Street (vegan options, wacky decor, DJs spinning turntables from a perch on the wall) .... and talked for three hours with the help of Côtes du Rhône, sushi rolls and a brie/garlic plate. We made a pact to always be frank with one another. Then he gave me a ride home and a satisfying goodnight kiss.

What's not to like? I believe we will go out again.

This is a personal milestone. If you had asked me even a couple weeks ago whether I would enjoy a romantic evening with a man 20 years older....

Hmmm.

The best way to couch it, I guess, is that there is something said for a man who knows what he wants, has already gone after it, and continues to go after it. In this case, the "it" being me. And he is going after me with style and the wisdom of his experience.

Stay tuned.

Approaching: older man

So the recent Craigslist classifieds approach seems to have borne slightly more fruit than my ailing tomato plant.

Last week I posted a request on their personals board. I kept it as bare-bones as possible: looking someone to hang out with, as it was getting quiet in my life with just me and my cats. Thought perhaps the lack of specifics might encourage creativity and a wide pool of applicants.

As you might well guess (and if you frequent Craigslist, are totally not surprised), this tactic attracted two-dozen responses from all kinds. Many asking about my current state of dress or undress. Many on the tactlessly graphic side....in some cases photographs were attached.

However, standing at the end of the pack is a gentleman with whom I may very well have a drink with this week, at his request. He knows my age....it was a headline in my posting. I don't know his, but if his picture tells the correct story, I'd guess.........maybe 50?

You read it here.

Yes, changing the tune. But our correspondence has been worthwhile--somewhat scintillating without spilling over into crassness. He's run eight marathons, likes to go out for breakfast, and spent last weekend cycling 40 miles through Franconia Notch. His initial response to my ad was to ask

"what is it that you want? I'd be interested to know why you posted the way you did..."

Ah, the way to a woman's heart! Or so we shall see.

New approaches

Ah, finally some summer weather to sink teeth into. 80 and sunny and no humidity....Singing Beach, finally!, you are my date for tomorrow....goodbye pasty-white legs.

So this reveals New Dating Approach #1: putting on a two-piece suit and going out in public.

New Dating Approach #2: Craigslist Personals.

Yes. I could not find a more less-measured or less-personal approach to finding someone than the free online classifieds. Simply say who I am (woman, 35, South Boston) and what I would like to do (watch the Red Sox game over a beer on a shaded patio, for example).

No profiles. No pictures. No need to state occupation or religion or what you last read. Say what's on your mind, wait about 10 minutes for it to be read, see who else wants to do the same, and choose. Remarkably efficient and no different than standing in a bar scoping the territory.

It's the center of July. This approach would well-suit a week in which I feel adventuresome. And when spending any prolonged time at my computer looking over profiles and composing witty answers seems a pasty-white way to be. Craigslist is quick. Random. More fleeting, perhaps, but an opportunity to practice on-the-spot flirtation skills......which would also serve me well for when I'm at the beach, trying to catch the eyes of the passerby.

I'm not suggesting the classifieds are an antidote to my singleness or even viable. However, while the Match.com men make up their minds instead of just looking and I make up my mind whether I'm too clever for most of them (or simply need to work harder at the game).....it is a temporary diversion.

Just mixing it up and, perhaps, stepping it up?