Thursday, February 28, 2008


Slightly drunken, nay… tipsy… blog post.

WOW, is all I can say about my date with the FOF / Friend of a Friend tonight. An amount of closeness / intimacy / passion / hotness I did not sense AT ALL on our first date. (note: tonight was the date that had the potential to just be of a platonic nature). All this in a cozy wine bar.

There was an invitation (and yes, strong temptation) to spend the night at his place, with promises that we’d keep a level of chaste-ness. Oh man. So tempting. I was (mentally) about 90% there, in the mindset of WHY THE HELL NOT???

Then the other 10% won over, and I came home – alone. I think it was the idea that anticipation in itself can be incredibly sexy. And I didn’t want to be in the position tomorrow where I’d be wondering if I’d hear from him again, wondering if we’d done too much, too soon.

But oy – that feeling of wanting to be “in the moment” and wanting to roll with it? A very powerful one indeed.

Sober point of view to come next time.

UPDATE: he e-mailed the next morning to say he'd had a very nice time, and was I free to get together for dinner next week?

(somehow, I have a hard time imagining that he would have sent this same e-mail if we'd spent the night together)

Monday, February 25, 2008

The pros and cons of serial dating

** Good for the ego. There’s something to be said for looking at your calendar, and realizing you have five dates lined up in the next week.

** More possibilities = more chances to meet someone you just might jive with.

** I tend to project a bit too early (if I really like a guy, by the second date I may find myself wondering, hmm, would we eventually move into my place or his?) – having other options / distractions helps me turn down the crazy a little bit.

** It can become easy to forget what stories have been shared with which guys. One time, I was IM-ing with a guy I hadn’t yet met (we’d exchanged a few e-mails) – and I told him I hoped he was feeling better, thinking he was a guy who had been sick earlier that week. He called me on it – and did NOT have a good sense of humor about it.

** Even an hour spent on a bad first date can be agonizing – time better spent at the gym, or with friends / family, or volunteering, or just about ANYTHING else. However, I’ve gotten better at trusting my gut, and realizing that no connection by phone generally means no connection in person.

** These dates generally involve alcohol and sometimes food – too much of both (and fewer nights at the gym) can quickly lead to a few extra pounds.

** The tedium of telling yet another new person about your work / life / adventures, etc.

Man update – recent dates:

Fun Bobby: we had a second date – dinner, a cocktail lounge. It was a fun time, with a bit of smooching at the end of the night. He seems quite keen, asking to make plans for the next date even before the night was over, then e-mailing me after he got home. However, these days, I’m allll about taking it slowly. And I’m trying to keep in mind that, in my experience, guys who come on super-strong fade away just as quickly.

One day at a time – anyway, I’m too busy at the moment to see him for another week or so.

Neighbor Dude: date #107. I had a great time with him, and I’d definitely see him again – but I just need to wrap my head around the fact that looks-wise, he’s not my usual “type”. I’m trying to keep an open mind – since I haven’t had much luck lately with guys who supposedly are my type, then maybe it’s time to change the idea of what my “type” may be?

He certainly IS my type in that he seems smart, fun, funny, and open-minded. AND he lives nearby, and shares my enthusiasm for exploring different facets of our wonderful neighborhood. I know, I know… I don’t need to decide today if I’m going to marry him. Simple question: would I like to see him again for another date? Simple answer: yes. That’s all I need to think about right now.

I’d love to hear your thoughts – what do YOU think are some pros / cons of serial dating?

Thursday, February 21, 2008

When it rains...

Truly – when it rains, it pours. I have quite a few dates lined up in the near future – there’s a chance that I may become overwhelmed – or at the very least confused as far as what stories I’ve shared with whom. But at this point, I’m feeling quite flirty and non-committal, so my plan is to have fun while it lasts.

The current lineup:

Earlier this week, I went on my 106th first date since my last serious relationship ended three years ago. Date #106 was with Fun Bobby – it was a very easy-going, good time. I felt as if I’d known him for longer than the few hours we spent together – but I wonder if I’m projecting – he looks a little like my friend, Good Hair Guy. (I’ve given him this moniker of “Fun Bobby” because his profile indicates that he’s a little unsure if he’s looking for a serious relationship right now – I’ve considered myself warned!)

Within a few days he e-mailed to say he’d had a lovely time, and asked if I was free to get together again this weekend. Plans are in place.

Then there’s Good Voice – date number two is set for next week. I can’t help but compare him to TC, who was in limbo with his career, and felt that that translated to his overall life (including dating). GV is very much together – quite successful, in fact – and this is refreshing in comparison. I certainly would never date a guy just because he was well-off – but I feel that I’ve reached a certain level of success in my career, so it’s not unreasonable to want the same in a potential partner. (obviously, he has many other qualities that I like – otherwise, I wouldn’t be considering a second date with him!)

Another newbie is Neighbor Dude, who lives just a few blocks from me. Good connection so far via e-mail and during first phone convo – plans are in place for this weekend. It’s hard to get a read on his pics – one is rather attractive, the other, less so.

Then there’s U.N. – remember him, from last summer? We’ve been in touch recently, and have plans for a drink next week. I have a feeling this will be a platonic get-together – BUT I liked him as a person that last time (just didn’t feel that ‘zing’) – I’m willing to take another chance to see if there’s any chance of zing. If not, he’s the kind of person I could see keeping as a friend.

One more: the FOF – Friend of a Friend (note: I initially gave him a different name, but worried that it might be too identifying). Background: we had one date last month, but he said he needed more time “off” after his recent breakup. I respected that, and appreciated his honesty. I wrote to him recently with a work-related question – after a few e-mails, we made plans to meet for a drink next week. I’m going into this with the mindset that it may just be platonic – but if something were to happen? That would be a nice bonus – I can’t explain it, there’s something I like about this guy. Maybe it’s because we have a friend in common, which makes him less anonymous than the guys I meet through the internet?

Oh – I have my eye on one more: I’m going to call him McLovin. My friend C is friends with him, and thought he’d be my type – when I checked out his MySpace page, I immediately fell in “like” with his pictures (as much as a sane 30-something reasonably can!). Great head of hair, nice smile, that Jewish New York look that I tend to go for. I just need to get more info on him. (C, if you’re reading this – let’s discuss soon!) There may be a possibility of a group outing in the near future – less pressure that way.

More thoughts / details on serial dating to follow!

Sunday, February 17, 2008

She's back!

I’m back from my South American business trip -- it was a great time, not as stressful as past business trips have been. Too much booze and meat consumption, however!

Alas, there were no encounters with sexy South American men, but there was that fun night with Quasi Ex during my stopover…

As expected, there just wasn’t enough time together, only a few hours – but the time we did have was incredibly hot. I don’t see him as boyfriend material, but it would be nice to get together more often for a spontaneous tete a tete. Alas, he’s a three-hour flight away.

In other dating news:

Good Voice: we had that one good date (#105), then I went out of town – and this week he’s away, but we made plans to get together when he gets back. He made it pretty clear that he’s looking forward to a second date.

Other New Guy: we have plans for this week. His profile seems to indicate that he’s not looking for anything serious at the moment – and I feel that I could use just a bit of fun for now – so from here on in, let's call him Fun Bobby.

Young Musician: I haven’t decided what to do about this situation yet. I could meet him for a drink, and just see what happens. Could be interesting, yes?


Would love to get your thoughts on this: (as usual, I’m overthinking things!)

When TC and I ended things over a month ago, I told him that I’d like to possibly be friends down the road, but for now, we should just have some distance. He said fine, best of luck, etc.

Well – I was pretty surprised to get a mass e-mail from him the other day, reaching out to his friends in his search for a new apartment. I mentioned it to a friend, adding that he probably just sent it to his whole address book – her response was that this sort of thing is seldom an accident. He could have easily have chosen not to include me in that list. In NO way do I think this is an effort on his part to rekindle things – but still, WTF?

One thing I do know for sure – it jolted me a bit with the realization that I’m not entirely over him yet. Crap. These days, I find that I don’t think about him that much, but when I do, it leaves me feeling quite melancholy.

For the record, I have no plans to respond to his e-mail. Not now.

Friday, February 8, 2008

Hello, Giddy!

A very quick note, as it’s late at night, and I should be packing for my business trip… but I’m too giddy!

I’ll get to the giddiness in a moment – but first, this week’s Dating Updates:

Good Voice: date went well the other night – we had a really nice connection, and I heard back from him already, saying he’s looking forward to seeing me again.

Other New Guy: don’t have a name for him yet – we had a fun phone conversation, and have already made plans for when I’m back in town. From his profile, I sense that he’s not looking for anything serious, which could actually be OK for me at this time.

Musician: speaking of fun… THIS could be an interesting situation: I got an e-mail from a very lovely-sounding guy who is, ahem, 12 years younger than I am. It was the picture of him with his shirt off that got to me – perfect, sculpted body. Really, the type of body that inspires fine art. So far, we’ve e-mailed a few times, but I’m keeping my guard up – I’m almost waiting for the joke to be revealed. I mean… my real age is listed on my profile… ? Are guys at that age really interested in women my age? (IF anything were to happen, I only see this as a fling possibility – and would be 100% honest about that with him.)

Now – for the giddy-making news:

I’m leaving on a business trip tomorrow, which (because of last-minute flight changes) now involves a five-hour layover in Other City. I happen to have a Quasi-Ex in this city. “Quasi” because we dated on and off when we were about 25, but were never quite BF/GF.

Gradually lost touch and stopped dating. About 4 years ago, he called me out of the blue, saying he had moved out of town, but was back in NY on business, and would I like to meet for a drink?

I was in the midst of a serious relationship at that time, and told QE this – we still decided to meet up. We were on our best behavior, but there was definitely a “zing” there, even without any physical contact.

A year later, I was single – got in touch with him again, and we talked about one of us planning a trip to visit the other. Finally, months later, I had a week-long work trip to his city – we were inseparable the whole week. And yet, by the end of the week, I’d had enough. Maybe I’ll elaborate another time, but I felt that our “relationship” had run its course (at least for the week).

Sporadic e-mails here and there after then. Until yesterday, when I found out that I was going to have five hours of down time in this Other City. My e-mail to him got a very enthusiastic response. A few e-mails later, some catching up on the phone... and I’ll just say that tomorrow night can not arrive quickly enough. Alas... it's sure to be the shortest five hours ever in the history of time.

I know I often lament being single on these pages. But times like this? Makes it all worthwhile.

Very giddy-making indeed!

Monday, February 4, 2008

Party: YES. Speeddating: NO. Giants: YES!

Went to a kick-ass house party last night with a bunch of friends, hosted by a (very) casual acquaintance, T, in his new downtown loft. Lots of beautiful, interesting, friendly people.

Sidenote: at this guy T’s last party over the summer, I exchanged numbers with three different guys.
Guy #1: never heard from him.
Guy #2: texted me the next day, asked if I was free for a drink that night – I wasn’t, but texted back, how about later in the week? He texted: he couldn’t plan that far in advance – four hours was already difficult for him. Needless to say, we never communicated after that.
Guy #3: walked me home, and we smooched along the way. At that moment, he was eager about getting together for brunch the next day – never heard from him again.

Funnily enough – ran into Guys #1 and #3 last night. Guy #1 recognized me (on line for the bathroom) before I realized who he was – he said something like, “remember me? We exchanged numbers, but never contacted each other.” Me: “oh, yes…”. The bathroom became available, I told him I’d catch up with him later, and that was that.

Guy #3: saw him in the lobby as I was leaving – he was with a very drunk girl. I decided to have a little fun, and said, “hey, weren’t you at T’s party over the summer?”. He smiled, and said, “yeahhh!”, very clearly recognizing me. Some small talk, and I left.

While at the party, I chatted with a cute guy who recently moved here from California (I probably wouldn’t have talked to him if it weren’t for my friend C, who practically nudged me into his arms – from now on, she’ll be known on these pages as WW: WingWoman). I offered to share some of my “secret” city spots with him, and we exchanged numbers. There was just something very appealing about him… here’s hoping I hear from him!

I had signed up for a speeddating event last year, but had to cancel at the last minute. I’m still on this particular company’s mailing list, so when they sent an offer for me to speeddate tonight for free (they were short a few women), I decided to give it a shot.

Caveat: it was Super Bowl Sunday.

I really couldn’t care less about football, and had no plans for the occasion – I was really curious to see what kind of guys would also be disinterested in perhaps the biggest sports night of the year.

Oy vey. I found out: not the kind of guys I want to date.

The age range for guys was supposed to be 35 - 48 -- most of the guys were well on the upper end of that, with one guy probably pushing mid-50s.

Talking to them, most were perfectly nice, even somewhat interesting. But looks-wise? The very opposite of whatever “type” I might have. From the big, bearded guy in the big sweater, to the eccentric aging-rocker guy, to the super-thinning-hair / droopy-eyed guy. There was no one I was remotely attracted to – I’ll leave it at that.

Super Bowl:
As I was walking home, I popped into a packed bar where the Super Bowl was in its last minute -- it was actually fun watching the excitement of the crowd, as I chatted with the sweet and cute (though not really my type) bouncer. Stayed for the end of the game – I enjoyed watching everyone hug and high-five each other.

THAT was the highlight of the night – it means nothing to me that the Giants won, but I’m happy for people like my stepfather who will be thrilled. It was one of those exciting New York moments that I love.

Plenty of Fish / POF update:
After weeding through lot of cheesiness, I have my first POF date planned for later this week with a guy I’ll call Good Voice, for obvious reasons. Had our first phone conversation today, and so far I like what I’m hearing. He’s a little outside my usual age range – I generally cap it at about 5 years older than me, and this guy is 8 years older – but he’s incredibly active, and is probably in far better shape than I am. I’m really curious to see what he looks like – one pic is promising, the other less so. As always -- wait and see!

Friday, February 1, 2008

Plenty of (stinky) Fish

I promised myself that I’d hold off on dating for a few more weeks – at least til mid-February, after my next business trip. And I just may still do that – but in the meantime…

Remember UN? We dated for about two months last summer, and while I enjoyed his company, I questioned whether I felt enough of a “zing” to continue dating him. Then I met TC, and things became much clearer – I ended it with UN, but felt that we might be able to stay friends down the road.

I recently wrote to him, asking him to return some DVDs I had loaned him. (also added some niceties – happy new year, and all that). A few e-mails later, and we’ve made plans to meet for a drink next week (where he’ll ostensibly return the DVDs).

I can’t help but wonder if anything of a romantic nature will happen. After all, I did have a good time with him last summer – we have a lot in common. And of course, hindsight being 20/20 and all that… when playing the “compare the exes” game, in many ways, he’s a better fit for me than TC was. In some respects (that I don’t want to get into here), TC was 30-something going on 20-something. (and yes, this was in the back of my mind while we were dating, but I didn’t want to allow myself to acknowledge it at the time!)

Enough over-analyzing! Ack, when given a chance, my mind wanders like a five-year-old in a shopping mall. Chances are, the drink with UN will be just that, with a platonic hug goodnight, and my DVDs in my hand.

In other dating news… I haven’t felt the desire to commit financially to J-date or Match just yet, but I’ve been doing a bit of browsing, and haven’t been very inspired. As I wrote to Cute Jewess – I feel like I’ve already gone out with half the guys that pop up on J-date.

Not long ago, someone here suggested trying one of the free dating sites, like Oy! I’m still trying to keep an open mind, but so far on POF I’ve encountered:
(a) way too many pics of shirtless guys
(b) enough typos to give a high school English teacher a coronary
(c) the guy in the wife-beater, squatting in front of his convertible -- classy!
(d) off-putting pop-up ads, eg,

Amidst the above, as of this writing there are two guys who have caught my eye. Some e-mails have been exchanged, but no phone calls as of yet – stay tuned. I’m still feeling a bit dating/rusty – besides Skydiver, I haven’t been on a first date in nearly five months. Eh – like riding a bicycle, I’m sure.