Tag Archives: First dates

Context: Dates 31.6-8, 35.1-2, and 14.4

Before I get to telling you about Date 37, who deserves a solo entry, just a quick update on where I was at in the dating arena. As you might recall, Date 31 was the sadistic nice Jewish boy who loves country music (and the way I give head). He would be so appalled if he knew I was writing this! Hehe. Anyway, he and I fall into the friends-with-benefits category since we love having sex but know we’re not right for each other based on where each of us is in life (i.e., he wants kids/I *don’t* want any more kids).That said, like me and Date 5 (whom you might recall has porn-star-worthy anatomy), Date 31 and I have an understanding that if we find someone we think is a serious contender, the benefits part of our friendship will be put on hold (hopefully indefinitely, but, you know…this isn’t our first rodeo).

Anyway, here’s the sequence of my dates just prior to meeting Date 37:

Date 31.6–He comes over to my place in his work clothes because he has client meetings afterward. All I can say is, yum! I love seeing a hot man (especially one I know is going to give it to me and hard) in a suit. Have I mentioned that Date 31 is a financial adviser? Well, he is. He works for a nationally known investment-banking conglomerate, so we always chat about the market and such. So there we are, on the clock, at my place. He’s hot, I’m hot for him, and he spanks the living daylights out of me until my ass is various shades of black, blue, and red. Which means I’m out of commission for at least a week with anyone else if I don’t want them to know what a slutty freak I am.

Date 35.1–Coffee date with a guy I met online. Even though I’d sworn off dating Hispanic men, since my many friends who are married to them consistently deal with all sorts of jealousy and possessiveness issues, Date 35 was super hot, over six feet tall, already had kids (boys–which are my theoretical stepkids of choice), and worked in lucrative field (yet another guy from the profession that must not be named, actually), so I made an exception. After meeting him in person, however, I was on the fence. I detected an angry undertone to Date 35’s words–especially regarding his ex-wife–but he was definitely hot and I couldn’t help wondering how the sex would be with him. Being that I was still all bruised up from Date 31.6, though, I knew I’d have to take things slow with this guy if they were going to go there, giving my ass time to look innocent. But what do I do? Instead of taking my vitamins and laying low, the next day…

Date 31.7–On my way to meet a romance-writer friend (of the sweet, chaste variety–yes, there is such a thing!) to attend a literary event, there was just enough time to meet Date 31 for a quickie. Right beforehand, he sent me this text: I’ll leave the door unlocked. Please lock it behind you. I’ll be naked in bed waiting when you arrive at 4:45. Please don’t say a word. Simply take off your clothes and start sucking my dick. After sucking it GOOD for a little while, ask me nicely if I am ready to fuck you. If I say yes, just turn over in the doggie-style position and wait for me to whip and fuck you. See you soon!

Oy. What can I say? I think Date 31 liked the idea of resetting my clock on getting close to anyone else. But that didn’t stop me from going out on a second date with Date 35, since I figured I’d be waiting until at least the third date with him anyway, but…

Date 35.2–When Date 35 showed up in his luxury SUV at my place to pick me up to go out for a sushi dinner, I was wearing a skirt, high-heeled sandals, a dressy top, and a very pretty cardigan (no, guys aren’t that far off base when they say I’ve got a “librarian thing” going on). Date 35, however, was wearing nylon gym shorts, shower shoes, and a grungy T-shirt. I almost didn’t get in the car. “Oh, sorry!” he exclaimed upon seeing me all dolled up. “I should have told you–because I have to wear a suit all week for work, I don’t dress up on weekends. At all.” No shit, I wanted to say, since he’d looked really nice when we’d met for coffee. “Want to go up and change?” he asked. I hesitated, wondering if I should just call the whole thing off, but honestly, I hadn’t had sushi in a long time, and I was super craving it. “Sure,” I said. “I’ll just be five minutes.”

Mistake!!! To make a long story short, the sushi was great, but the conversation was questionable. Date 35’s deep-seated anger became more and more apparent as the night wore on, but at the same time, he kept ordering drinks for us and touching me in ways that were turning me on, despite my better judgment. After dinner, he said he needed to sit in the car for awhile before he felt like he could drive responsibly. Now, the right thing to do would have been to tell him to walk me home, since the sushi restaurant was reasonably close to my place. Instead, I said okay and hung out with him in his car, where he proceeded to maul me like a sex-starved teenager. No, I didn’t have sex with him, but he got way too up close and personal with my business. Luckily, it was dark, though, so he didn’t see why I was fighting so hard not to remove my clothes. In the days afterward, he texted me incessantly, wanting to take me out again. Because of his angry attitude, I hesitated to say no right away, kind of giving him the run around, but within a week, I manned up and told him sorry, I just wasn’t feeling it, and he left me alone.

Date 31.8–Knowing I was about to have oral surgery and my dick-sucking prowess would be impaired for at least a few weeks, Date 31 made a special late-night visit to my place mere hours before I was slated to show up at the periodontist’s office. It was the third time I had seen him in ten days, and I have to say, even though we were clear on not being serious with each other, it felt way too comfortable, like if we did ever decide to take things to the next level, we’d actually be pretty happy together. We talked about pre-nups, my kids, the stock market, after-hours trading, and whatnot. He ate my leftover Chinese food, then devoured a bunch of my homemade oatmeal-craisin cookies, exclaiming how fat he’d be if we were married. But what can I say? Different goals. At any rate, we parted on a good note.

Date 14.4–Have I mentioned that I’m a sucker for men in golf clothes? Not sure what it is, but I can’t help it–I get totally wet when I see hot guys in polo shirts, visors, and golf shorts or pants. Date 14, who was still 27 at the time, works for a major golf-equipment manufacturer and golfs a lot as part of his job. I was probably way too loopy from the painkillers I was on after my surgery, but for whatever reason, when he texted asking if he could stop by for a little while, I said okay, sure. When he showed up still wearing his golf clothes, however, I was like, right on!!!

What a mess. So, all that to say, I’m somewhat lacking in the self-control department. Both Date 31 and Date 5 had been telling me forever that if I liked a guy, I needed to NOT sleep with him right away, instead making him wait a bit. With that bit of wisdom in my pocket and my recent experiences–which proved I was going nowhere fast in the relationship department with how I was behaving–a couple days later, I went on a first date with a new guy: Date 37.

One-Hit Wonders: Dates 33.1, 34.1, 36.1, & 40.1

As I think I’ve mentioned, because Date 31 and I knew we weren’t ideal for each other, we had an understanding that we’d date other people but only sleep with each other. As a result, I went on a succession of Internet dates. First dates tend to be so fleeting, I’ve come to think of them in terms of cocktail-party conversation. Namely, I keep it light, keep it moving, and try to learn something in the process. That said, here’s the lowdown on how I fared in January:

Date 33.1 – An intelligent, handsome (but short–he barely cleared my height) gentleman in his late 50s, Date 33 took me out to dinner for our first meeting. Our conversation was lively and interesting the whole date through, and I found myself fascinated with this guy. At the conclusion of our date, he asked if I’d like to go out with him again and I said yes, hopeful he’d ask me to go sailing with him on his 45-foot boat. He kept touching me throughout our date (casually and appropriately, but also very intentionally), so I’m pretty sure he was attracted to me, but then he never called for that second date. Honestly, I don’t think I did anything wrong, since all the trappings of a successful first date were in place, so I have to chalk this one up to being about him, not me. Anyway, onward!

Date 34.1 – I had my doubts about Date 34 when I agreed to meeting him, since he lived over an hour away, but he seemed really nice, so I figured I’d give him a shot since he was in my area for work one day and asked if I’d like to join him for lunch. But here’s the thing: my instincts were correct. I hate to say this, but the area he lived in is kind of remote, and the fact that this didn’t bother him meant we weren’t a match. Not to mention the fact that he showed up looking ten years older than his pictures (this may equal laziness, rather than dishonesty, but either way, it equals both, which goes down as a minus in the date-evaluation process). Also, he was wearing a gold chain under his polo shirt. I know I’ve mentioned it before, but I’ve got to say it again: Guys, tread lightly when it comes to man-jewelry; we chicks don’t dig it unless it’s an expensive watch or your wedding ring (and you’re married to us!). Date 34 was a sweet guy, but like I said–we weren’t a match, so I declined when he came asking for a second date.

Date 36.1 – Surprisingly, Date 36 was the first Asian guy I went out with (surprisingly, because some of the worst crushes I’ve ever had have been on Asian guys; in fact, I lost my virginity to an Asian guy I had it really bad for back in high school). Super handsome and mega-smart (like I’ve mentioned, I go for brainiacs), Date 36 did not disappoint when I met him in person for coffee on a Saturday afternoon. But here’s the thing: he was mega-Zen, like the type of guy who surfs every morning and nothing can rattle him because he’s so perpetually blissed out from spending so much time in the water. I, on the other hand, have always secretly wanted the T-shirt Booger sported in the movie Revenge of the Nerds that read HIGH ON STRESS, since it so accurately reflects my personality. Plus, Date 36 went to Berkeley, while I went to UCLA. Now, the fact that we both went to top UC schools might seem like an argument in favor of compatibility, and it is in some respects since they’re both esteemed California public universities with student populations of similar sizes, but here’s the thing: Bay Area people tend to have something against us SoCal-ers. They’re smarter, but we’ve got prettier people and better weather, and they can’t seem to forgive us for it. Don’t believe me? Check out the local news any weeknight on one of the San Francisco Bay Area’s television stations. Any stories about Los Angeles inevitably portray the city (which is actually full of way more courteous, wonderful, hard-working people than the douchebag bubblehead types who populate the tabloids) as seedy and inherently evil. Plus there’s this level of pretension even former Bay Area folk sometimes carry with them. An example of how this plays out in its natural habitat is found at the Barnes & Noble closest to Berkeley, where they have a section labeled Thesauri. I mean, really? Can’t just lump them in with Reference, now, can we? Some of my closest friends are from the Bay Area and aren’t at all like this, but they also don’t plan on moving back north. Others, well, they’re going to remain acquaintances rather than friends, because we Southern Californians may seem laid back and simple, but we know when we’re being looked down on, and the snobs aren’t invited to the next party. Anyway, I could tell Date 36 thought I was a ditz and wouldn’t be asking for a second date. Turned out I was right. See? We SoCal blondes aren’t so dumb after all!

Date 40.1 – This date actually happened just recently, in May, but it’s of the same ilk, so I’m adding it to this list. That said, on paper, Date 40 seemed to have all the boxes checked: tall, handsome, well-dressed, good job, responsible homeowner. Conversation between us was lively as well. But there was an edge to Date 40, like he might have been a little bit mean, and like what he was really after was getting laid, not going out to dinner. I might have mentioned this before, but I have kind of a good-girl schtick going for me. Some guys (cads!) can see right through it, but most of the guys I’ve dated traditionally (if you can call online dating traditional, but you know what I mean–as opposed to bar-pickup/hookup dates) see me as a squeaky-clean, bookish, church-going mom-type. And I am all that! But I also very well might be a sex addict, so it’s kind of funny to me when guys dismiss me as too straight-laced or whatever and move on without seeing where things might lead given a couple glasses of wine and a tasty dinner. Anyway, Date 40 was one of those. Because he’s so tall and has money, I’m sure he has a vast selection of women at his disposal. Chances are, I dodged a bullet by letting him think I’m all prim and proper.

Such is life, right?

 

Date 32.1: Hit & Run

Feeling satisfied that I had a steady supply of sex on the horizon, I proceeded to date a succession of new guys, the first of whom was Date 32. Now, online, Date 32 looked gorgeous. His photos showed a tall, lanky, blond surfer guy with a nice smile and a kind of earthy disposition. Plus, in his messages back and forth with me, he was very nice. We had a phone call, too, but I was distracted by the fact that Date 31 was on his way over to my place, so I wound up cutting things short (and yes, I realize how very wrong that was of me).

Anyway, here’s the thing: when I went to meet Date 32 in person, I knew right away that he wasn’t for me. “Earthy” actually meant “poor,” and the laid-back surfer I was imaging actually turned out to be more of a beach bum, complete with a skeezy mustache and crooked teeth. Not wanting to be superficial, however, I said hello and shared appetizers with Date 32, since you never know–could be, my instincts were wrong. But it turned out they weren’t.

The longer I sat there, making conversation, the more convinced I was that I had to get out of there and never see this guy again. The stories he told me about his kids had me siding with his ex-wives (note the plural), and the way he looked kind of reminded me of one of my uncles, which wasn’t a turn-on. Not caring if you’re going to impress or offend someone, though, is a powerful thing. It tends to lead to blatant honesty, for better or worse, so this guy got to hear all about my faith, my church, my ex, and my struggles with my kids.

Did I know those are forbidden date topics? You betcha! Maybe I’m wrong, but I think being overly honest in an attempt to scare someone away is better than flat-out saying “No,” and then walking away, or taking a covert look at a date and then bailing (both of which have happened to friends of mine!). Maybe the over-honesty is a scare tactic, sure, but it’s also a last-ditch effort to give the person a chance. Because what if you get to talking about all those touchy subjects and then learn that you actually have some rapport with the unlikely match? Could happen. In this case, though, it didn’t.

Date 32 never called, texted, or messaged me again. Guess neither one of us was feeling it.

Dates 12 and [-4]: The Telephone Is Your Friend

Last night, even though I shut my dating-website profile down (again), I received a call from a guy I’d briefly traded messages with a couple weeks ago. I felt kind of bad about not remembering him better (“What’s your name again?” “How old are you?” “Oh, yeah–the straight-edge/agnostic/vegan guy with the one-hit-wonder-’80s-band screen name. Now I remember you!”), but we had a nice conversation anyway.

Although I kind of doubt we’re ever going to embark upon an actual date, we had an interesting discussion regarding the peculiarities associated with online dating. When I related to him how I’d been stood up on a coffee date this week by Date [-4] (who, in hindsight, I’m strongly suspecting is actually that same lesbian chick who played me twice before), he asked, “Didn’t you talk by phone first?”

“Um, no,” I was ashamed to admit. But then, about half of the dates I’ve gone on haven’t involved phone conversations beforehand, just an exchange of email and/or text messages. Not to mention I have talked to certain guys beforehand, but then meeting them in person was a total bomb (see Date 1.1). Some guys just aren’t as comfortable chatting by phone, so the fact that Dates 2, 4, 5, 7, 8, 9, 10, 11, 12, 15, 18, 21, and I didn’t converse telephonically before our respective first dates didn’t strike me as odd. Now, however, I’m starting to learn.

Better late than never.

Because, let’s pick apart the above situations…

Date 2 – If I’d insisted on his calling, he’d have declined, because I’m pretty certain (after the fact) that he’s married, so sharing his cell phone number (because I’m also pretty sure he’s an amateur, part-time cheater, not a guy with a secret disposable cell phone for extramarital escapades) would have been a no-go. Now that I’ve moved back to my previous suburb (where Date 2 also happens to live), I’m just waiting for my opportunity to make him sweat. One of these days, we’re going to run into each other at a school or social event. I won’t rat him out, but I will say something like, “You look familiar. Where have we met? I can’t quite place it…”

Date 4 – Extremely resourceful and horny, if I’d insisted on a phone call, Date 4 would have made it happen, so maybe he’s not the best example of why this should become a nonnegotiable dating policy. Plus, he called and face-timed me after we were already dating, so even though he wound up being kind of a flake, I really don’t think he has anything to hide. Then again, maybe he’s still married, too, and not in the process of getting a divorce, like he said. Never can tell, especially when someone just up and disappears.

Date 5 – Just in case he happens to be reading (since he’s one of the two guys who know about this blog), I’ve got a message for him: I love you, babe, but you’ve got intimacy issues. Had I insisted on a pre-initial-date phone call, I might have been able to sniff out this fact. Maybe it’s just me Date 5 doesn’t want to get close to, but his hardcore avoidance of real-time phone conversation makes me wonder what’s going on beneath the surface. Could be why a great guy like him is in his late 30s and has never been married. Just saying.

Date 7 – If I bored (or overwhelmed?) him so much he didn’t want to go out with me again, and all we did was have drinks, appetizers, and conversation together on our first date, perhaps we could have scheduled a phone call beforehand and skipped a step? Again, just saying–everyone’s time is precious.

Date 8 – Guy was legit, so a pre-dating phone call wouldn’t have changed anything. However…he was late to our first date, and we’d only been communicating by email prior (and I didn’t yet have a smart phone), so it would have been nice if he’d called to let me know he was caught in traffic but on his way.

Dates 9, 10, & 11 – They probably would have called if I’d insisted, and then I’d be more clued in about their personalities and priorities. Not a dealbreaker, since I’m usually up for meeting new and unique people, but also not a bad thing when you’re agreeing to meet a stranger off the Internet for the first time.

Dates 12, 15, & 18 – Could have saved myself some trouble if I’d talked with these guys beforehand. Dates 15 (communication-scrambling accent/rotten tooth) and 18 (sex maniac/control freak), you know about. Date 12, I’ll get to in a minute.

Date 21 – Not sure a phone call would have changed the outcome, but at least I’d have been forewarned about how passive he wound up being, which didn’t ultimately wind up giving me what I was looking for that night.

If I had engaged in a longer telephone conversation with Date 6 (he kept catching me as I was running out the door, so we never got to talk much before meeting in person, though I have to give him credit for trying), I would have known that (like the guy I chatted with last night), he laughs like Scooby-Doo. I also would have gleaned how freakin’ boring his life was (like another random guy I’ve met online, talked with on the phone, but have no plans to ever meet in person), so I might have nixed our plans and saved him a drive from East County.

But let’s get to Date 12 already, shall we?

All right. This is going to make me sound like kind of a mean person, but I want to tell it like it is, so here’s the thing: Date 12.1 was probably my worst date ever.

Before I get to what made Date 12.1 so bad, let me just say that, as an nonphotogenic individual (almost all my dates have told me I’m better looking in person–still trying to decide whether this is truly a compliment, since I think the pics I’ve posted are accurate and decent, but whatever), when I see guys’ pictures online, I tend to give them the benefit of the doubt. That said, on paper, Date 12 sounded like a stand-up guy: good job, already had a kid, my age, reasonably active lifestyle, etc. His photo, however, wasn’t the greatest. In fact, it made him look downright ugly. Because he had only posted one picture, though, and it was kind of blurry, I just figured he must be new to the online dating scene, not realizing the importance of a flattering image. Aw, I thought, that’s kind of sweet how he’s so clueless. I’ll bet it’s just a bad angle.

But it wasn’t. He looked exactly like he did in that picture when I met him in person. In fact, he almost looked worse, with deep wrinkles crossing the bridge of his nose, making me positive he’d lied about his age, since there was no way this guy was in his early 40s. Late 40s is more like it, I thought, but really, I was prepared to hear he had already begun his 50s.

Compounding my issues with his looks was the fact that he had way too many buttons unbuttoned, revealing (get this–I’m not joking) a gold chain around his neck. Now, in his defense, he grew up in New Jersey. But here’s a tip for any East Coaster guys who might happen to be reading: we don’t do this in Southern California. Not since disco was popular, anyway.

I’m generally a pretty friendly, nonjudgmental person, though, and in his pre-date texts, he’d asked me what kind of wine I liked. I told him, and he said he’d have a bottle ready for us when I arrived. Nice gesture, right? So even though he wasn’t Prince Charming, looks-wise, I figured we could still enjoy a worthwhile evening.

But then he opened his mouth. Within two minutes of meeting each other, we were already fighting. How do you start an argument with someone you’ve barely met? you might ask. In this case, it started with a discussion of public-school API scores (a standardized testing measurement employed statewide in California). I don’t want to call out where I live, but the schools in my area have the highest scores in the county. This is a fact, one backed by data available on the California Department of Education website. But this guy wanted to argue with me that the schools in his neighborhood were better (although his ex-wife lives in my district, so let’s all do the math here).

Moving on, conversation got creepier and more skeezy, with Date 12 alluding to the fact that he knew I was sexually submissive based on the dating-website personality questions I’d answered. Only with people I like, I wanted to point out, but I just kept changing the subject. In the course of finding benign things to discuss, the reason he looked vaguely familiar to me was revealed: we had been part of the same scout troop, meaning we had tons of mutual acquaintances.

Talk about making a bad date worse! Now, instead of just being able to get up from the bar and leave, channeling my inner bitch, I had scores of people to answer to for my behavior. This is why I enjoy online dating so much–if it goes badly, there aren’t any real-life social repercussions. In this case, however, I had to find an alternative means of escape.

I decided to broach all those subjects people aren’t supposed to talk about on first dates: my divorce, my custody battle, the kid from scouts who died of cancer, the heart-crushing details of his funeral. Yeah, I know it was wrong for me to exploit that kind of information, but I kept shooting pleading glances at the bartender at the same time, trying to telepathically send him the message, Check, please! Only the bartender kept ignoring us, finally bringing over the tab after three grueling hours of disastrous date time.

The worst part, I have to admit, though, was when Date 12 asked me about my astrological sign. “Yes, I’m a ________,” I admitted.

After asking what my actual birthday was, he wanted to know, “And you’re really 42?”

No, I’m really 36, I wanted to say. I just tell people I’m 42 so they’ll think I’m more mature.

“Yes,” I assured him, then asked, “What about you?”

“You’re not going to believe this,” he said, digging into his back pocket for his wallet, then producing his driver’s license for my inspection.

Know I don’t like to cuss, but, Fuckin’ A!!! Dude had the exact same birthday as me. Exact same year and everything.

You, me, and [insert name of goofball hair-metal-era lead singer who’s repeatedly been kicked out of his band], I couldn’t help thinking. No one cool ever has my birthday!

Date 12 tried to get me to go back to his place with him after we left the restaurant, using smooth lines such as, “I really didn’t think I was going to like you.”

Yeah, well, thanks but no, thanks, I wanted to tell him. Because we had so many mutual friends, though, I made excuses about having lots of work to do and drove away vowing never to see him again. He did, indeed, wind up asking me out again, but I pulled the Date 17 card, saying someone from high school had recently come back into my life, and I wanted to see where things were going. True, that, but still–sometimes it’s best to just shut up, be diplomatic, and chalk the whole thing up to being a learning experience.