Taking Third-Date Sex to a New Extreme
Benita and I were enjoying a Friday night dinner together in a cute little French bistro in San Francisco. Our one other date had been simple and fun – flirting and getting to know each other over cocktails. That first night we’d pecked cheeks when we met and kissed briefly goodnight, so I didn’t know what to expect for date number two. A make-out session seemed likely, but she lived with housemates and I didn’t think she’d take me back to her place. I lived an hour south.
Which posed a problem for a future date number three – that magical time when sex was most likely. As a divorced single dad with shared custody, my next free Friday night wouldn’t be for two weeks. The distance between her City apartment and my Silicon Valley home made sleeping-over midweek a challenge.
But Benita was Brazilian and prided herself on her sexual freedom. I wondered if sex maybe didn’t have to wait. Bad idea, I know, as far as developing a relationship was concerned. Then again, even first-date sex can occasionally lead to something lasting. The number of the date takes a back seat to feelings. As much as I wanted to get laid, I also thought Benita and I had long-term potential.
“Want to go wine tasting?” I asked. Napa wine country was an hour north-east.
“I love wine,” she said. “When were you thinking?”
“This weekend.”
“Hmm,” she said, considering the idea. “I’m free tomorrow. But that’s a lot of driving for you.”
“We’ll leave tonight.”
Her face eased into a sly smile, and I knew I’d hit the mark.
“Let me guess – you have a packed suitcase in your car,” she said.
“Nope. This is spur of the moment. I’ll wear what I’m wearing.” I held my arms wide.
“What about brushing your teeth?”
I flashed a toothy smile and shrugged.
How a woman can determine so early on whether a guy is a good one, like me, or a freaking psycho is beyond me. But Benita went with the plan. Upon leaving the restaurant, we jumped in my car, pit-stopped at her apartment, and headed to Napa.
On the drive she asked if we were getting one room or two.
“Um, one?” I asked. “Or two, if you’re uncomfortable.”
“One’s fine. One bed, too.” She squeezed my hand.
Oh, my.
We found an inexpensive hotel on the south side of town. It wasn’t a spa, just standard accommodations. And with only one bed we didn’t get a whole lot of sleep. By choice.
Entering into a relationship post-divorce is often hard, especially when other dating relationships haven’t panned out. But over breakfast the next morning, I had the feeling Benita and I would make a good couple. She was my type of woman – educated, cute, athletic, compassionate, free-spirited. Not to mention, a rock star in bed. I felt at peace, like we weren’t rushing a thing. Life had come at us and we’d worked with the time we had.
She must have felt it, too, because while I poured syrup on my waffle, she told me she liked me a lot. She wanted to make space in her life for me.
“Just promise me, David, you’ll never tell me about your affairs with other women,” she said.
“There aren’t any other women,” I said. “I date one woman at a time.”
“Oh, come on. Everyone has lovers. Even the lovers have lovers in Brazil.”
Sigh. Turned out she had lovers in San Francisco, New York, Rio. And she knew that those men had other women in their lives.
Polyamory isn’t exactly my cup of tea.
“If we dated seriously, would you still have lovers?” I asked.
“Yes,” she said.
I hung my head, stared at my syrupy waffle.
“We can’t be boyfriend and girlfriend, anyway,” she said. “You have kids, and I don’t want to be a mom. But we can date for fun and be lovers.”
Hello – wasn’t that something she might have told me on date one or two?
“You didn’t ask,” she said.
“Then what are we doing here?” I asked. But I knew I’d brought it on myself.
“You invited me wine tasting. It sounded like fun. Whatever happened last night in bed couldn’t be controlled.”
She was right about that.
And I guess third-date sex should probably wait for date number three.
(There’s more to this story, but I’ll save the rest for a future post… )
- How to Start Dating a Single Dad
- Dating Tips for 40-Something Men
- Sexy Flirty Dirty Text Messages
- Hot, Sexy, Confident
- Virginity? It’s So Overrated
- Nude in Chains (An Actual Date)
- What’s More Natural Than Nature? – Confessions of a Serial Online Dater, part 3
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Entries
Comment by Tonya
| August 6th, 2008
Oh!! I was getting so excited about all of this!! What a great post!
But on a good note, you did get some Latina lovin’ and I know that’s gotta be HOT!!! (speaking from someone who has Latina heritage) :)
I can’t wait to hear…. the rest of the story
Comment by Cathouse Teri
| August 6th, 2008
This took me aback. First, you are actually PLOTTING how to arrange a third sex date, because that is when sex is likely to happen. Second, you are confused about a woman who has several fuck-buddies? Is this a true story? Is this really how you think? Pondering when and where the sex will happen? And when it does, you are shocked to find out the woman is not prepared to be in an exclusive pre-relationship with you, as a fuck-buddy or otherwise?
I have no idea how to interpret this. It makes you seem like a conniving, yet desperate man, who is looking for love in all the wrong places.
Relax, man!
Comment by Honey
| August 6th, 2008
That’s disappointing, DM. Though it’s kinda what happens when you like someone enough to project your hopes onto them rather than discuss it with them.
Comment by debra
| August 6th, 2008
Why is this conniving? Sadly, with geography and schedules of busy adults, especially parents, you’ve got to think ahead sometimes in order to set the scene for what you’d like to have happen. I think David is a genius! What a great, spontaneous suggestion to leave that night. When you’re looking at a finite amount of time, and know that your next opportunity to get together may be more than 2 weeks away, you strike while the iron is hot! I have a similar rule; 3rd date, but I layer on the regret clause, meaning, I have to decide, for myself, will I regret sleeping with him, or will I regret NOT sleeping with him. I’ve been lucky, I’ve been informed enough to make the right decisions most of the time.
I don’t think that DH was either confused or shocked by learning Benita has multiple partners, I think he was simply disappointed. Disappointed to have met a women that was appealing to him in alot of good ways, and disappointed to have not learned of the deal breakers sooner. But you have to ask yourself….sometimes, even when you know there are dealbreakers, but you still have a great time with someone, are really attracted to them, enjoy and respect them, you still make the same decision as if you didn’t know about the deal breakers. A spontaneous, exciting trip to napa with someone I’m that attracted to…deal breakers or no, that’s a situation where I would have regretted NOT sleeping with a man.
Comment by Cathouse Teri
| August 6th, 2008
Debra ~ I am a busy adult and I am a parent. When I go on a date, I simply enjoy myself. If sex happens, great. If it doesn’t, no big deal. When all of that thought and pressure is added, it tends to make dating into a chore. Which is exactly what I read from just about everyone as how they view dating. They can’t WAIT until they find that special someone and can stop the damn plotting and planning charade! They can stop guessing what he/she will like and when they will like it and just HAVE someone.
I am not at all inclined to encourage that kind of thinking when it comes to dating. It’s detrimental at its foundation.
But hey, what do I know?
Comment by laurakim123
| August 6th, 2008
Is there a 3rd date sex rule? I really had no clue!
Well at least you did get laid I suppose but perhaps maybe next time ask what their intentions are on date 1?
Comment by The Exception
| August 6th, 2008
It sounds like you wanted more from this situation - and hoped for more, but honestly, it sounds like a blast! Talk about living in the moment! She sounds like she knows how to have fun - fun sex that is - no strings… just enjoys the pleasure of a man’s company for all that it is and the moments shared.
There is a book called Lust in translation that I want to read regarding the different ways cultures look at lovers, affairs, etc.
Comment by Single Mom in New England
| August 6th, 2008
Wow, David, that story woke me up at my desk — you never fail to disappoint. I think you’re living the life most of us daydream about having once in a while.
If I were Bonita, I have to say I might’ve driven to the wine country too - the spontaneity sounds so romantic -but unfortunately you didn’t have the female requisite pre-sex relationship talk BEFORE the sex — like, what are you looking for in a relationship? But you already knew that, didn’t you? And at least she was painfully honest with you. Now it’s up to you to decide what you want to do with it. Having another filly in your stable might help those lonely nights while you’re looking for your soulmate to come into your life… Okay, I can’t believe I just wrote that…
Comment by TentCamper
| August 6th, 2008
Dude…I don’t know whether to say damn…or DAMN!
I guess it is hard…esspecially when you are talking about someone from a culture that accepts “lovers”
Glad the sx was good…never a bad thing…but if you are looking for someone for a lasting relationship…I guess she may not be “the one.”
Comment by vinomom
| August 6th, 2008
I don’t think DH is conniving, I think anyone who wants to believe that romantic interaction with the opposite sex can be done with some planning, plotting, and just generally playing THE GAME is kidding themselves. There are degrees of all of this, some people take to the extreme, but if you don’t have at least a little bit of Game, I don’t think you will find yourself in any long term dating situations.
Comment by Single Mom in New England
| August 6th, 2008
Okay, now you’ve lit my imagination on fire… Let’s all guess what DH’s “rest of the story” is… I’m guessing it’s going to be titled, “The best places/wineries to have sex” as he may just take full advantage of the last day he may spend with this woman… :)
Comment by singlemomseeking
| August 6th, 2008
Oh, you and those olive-skinned women… sounds like one body part was speaking louder than any other?
Comment by singlemomseeking
| August 6th, 2008
P.S. I just read Single Mom in New England’s comment about your next blog title. I’m cracking up here in the library! Good one. She knows you SO well!
Comment by Kat Wilder
| August 6th, 2008
I gotta kinda agree with Cathouse on this one (not on the conniving/desperate part, though); it’s much healthier to go on a date or meet someone with no expectations. If you’re starting to feel that he/she likes you, and you feel the same, then that’s when the “what are you looking for, lover or partner?” should be discussed..
Although, if it flows in an organic way, someone who knows he/she’s just looking for NSA sex should be forthcoming. (and the STD/AIDs discussion, too)
My goodness; has it always been this complicated?
Comment by dadshouse
| August 6th, 2008
Teri - your comment took me aback. Call me old-fashioned, but I prefer monogomous relationships, even with a lover. I wasn’t shocked or confused that this woman had lovers because some of my single friends sleep around. But I was disappointed. Part of it is my values. Part of it is me having kids - I can’t and won’t parade a string of lovers in front of them. I want to bring a girlfriend around them. Did I expect this woman to drop everything for me that moment? No. But she clearly said she never would change, and that was a dealbreaker for me.
Was I plotting when I might sleep with this woman? During this second date - YES! As Debra points out, for single parents with custody schedules, figuring out when you’ll get to see someone is a big deal.
Also, believe it or not, Teri - men actually plot dates. We call ahead to a restaurant and make reservations, ensuring the ambience is right. We might plan two or more stops in the evening - drinks, dinner, dessert or nightcap. Ask Lance or anyone else, this is how it’s done. (I belive Lance refers to venue changes as “bouncing” locations) That is how dating works! If you aren’t aware of it, then the men you’ve dated have kept the magic alive and shielded you from all the planning, thought, and effort.
As for the Napa idea, it came to me during the dinner date. So it was spontaneous. We went with the flow and both had a great time. What is conniving about that?
As for expectations - this was our second date, and we had met on match.com, so yes, we both had some expectations. She knew about my kids but chose not to take a side until we got to Napa. Who knows why? Maybe she truly was undecided about kids until she spent enough time with me to realize parenting wasn’t her cup of tea (or at least step-parenting, she didn’t make the distinction) So I assumed from friggin’ match that she wanted a partner like me. Maybe a lover is her idea of a partner? Who knows.
I had a great time in Napa with this woman, no regrets at all. I was bummed she had no desire for monogomy. I didn’t expect anything, but had we at some point both chosen to date exclusively, then I’d prefer she only slept with me. She said she would never live like that.
Comment by Me Thinks
| August 6th, 2008
Wow, how is there a debate about this? Dadshouse, you certainly know how to stir it up!!!
” she told me she liked me a lot. She wanted to make space in her life for me.”
That to me is what is bothersome. If you met on Match, she knows you’re a dad and I would assume your profile indicates you are looking for a relationship (as opposed to ones that hint they are just looking for FBs or FWB) then I’m curious why she didn’t indicate that you were not BF material earlier? Very odd! So she is just collecting “lovers” (lets call them FWBs, that is what she wants)?
Anyway, I’d love to see what is in her profile, you should re-read it and look between the lines to see if you could have known this ahead of time. I’m sure there is something there.
But at the end of the day, my guess is that you would have done the same exact thing but without the hope/expectation that it could have turned into something more. Sounds like a really fun time but was missing some communication on both your parts. Live, experience, take notes, repeat until you get it right.
Comment by Single Mom in New England
| August 6th, 2008
Yes, MeThinks, she wanted “to make space” for him in her life… between the other two guys in her bed! Lol
Comment by vinomom
| August 6th, 2008
The fact that you met her on match.com makes me think differently. In that case, she had a pretty good idea of what you were looking for, and what she was getting into. I hate when people use relationship sites for hookups. If all you wanna do is hook up go to a bar. Match (IMHO) is to look for something a little more meaningful.
So now I kinda think that girl sucks.
And just to valifify my comments I met my BF on match.com so I speak from experience.
Comment by dadshouse
| August 6th, 2008
Me Think and Vinomom - I think there are quite a few people on match who are really there just to date and have fun, and not take it all so seriously. I’ve had women tell me they’ve met married men on match looking for affairs. Those men certainly don’t advertise their marital status. Maybe this woman didn’t advertise her true status.
I think she wanted a boyfriend/lover, but not marriage, and so maybe the fact I had kids was a non-issue to her. A lot of San Francisco singles NEVER leave the city (which is why I usually don’t date SF women). From their point of view, traveling to the peninsula, where I live, is like traveling to Siberia. So maybe this woman figured if we dated, I’d come to the City a lot without my kids, and my kids would never be an issue.
Comment by dadshouse
| August 6th, 2008
Oh, and “making space in her life for me” could have just meant she’d give me pillow space a few nights a week. Working me into her lover rotation. If she wants multiple lovers, fine for her, but I’d rather sleep with one woman and have her sleep with just me.
Comment by pajama momma
| August 6th, 2008
Dave was thinking like a man.
Obviously I’m generalizing,here but we all know men think about sex in different terms and more frequently than women. I just don’t see it as odd that he was hoping to score and figuring it’d be by the 3rd date.
I am glad, however, I got invited into the “boys club” with this little story and am now looking back at past dates in my life and cringing when I think of my third dates and knowing what my date was thinking. Of course back then, I’m pretty sure I assumed he was hoping to score on the first date.
You don’t have to be a single parent to have planned this kinda stuff. I was planning my wedding on my 3rd date with some of the dates I was on. Oh, so glad those didn’t pan out.
Comment by pajama momma
| August 6th, 2008
Danger, will robinson!
random comma alert!random comma alert!
Comment by Lance
| August 6th, 2008
Just picked up this thread. Lots of great material here and a great interaction.
As DM says, there’s a certain degree of planning and thought that goes into a good date. It has to have SOME structure and SOME thinking about the income so that it can be propelled forward, or else the interaction comes off as stale and directionless. I’ve had plenty of these and you know what chicks say? Oh, nice guy, but we didn’t have any ‘chemistry.’ There was no ’spark.’ Well guess what, that spark happens BECAUSE someone in the interaction (preferably both people) is massaging it towards a goal, and that goal IMHO should be sex, but it can be anything. The best way to get the sparks to fly is when both parties want it and work towards the same goal, ie flirting back and forth.
Comment by Lance
| August 6th, 2008
Also wanted to comment on Benita having multiple lovers. I respect DM’s monogamy values, but my perspective is that a fuck buddy SHOULD have other dates and other lovers. That guarantees that the two people won’t cross the FB line.
I’m not 100% convinced about full-on polyamory, but I don’t have a problem sharing her with other lovers as long as they’re out of sight and out of mind. In fact, I would encourage it if that’s the position she’s in. Some women just need to date and sleep around. Some guys too.
Comment by mama llama
| August 7th, 2008
This story cracked me up!
What I initially thought was, “Hmmm…funny how Dad fled when *she* was the one to propose a polyamoratory relationship.” I could be mistaken–I thought you had previously posted about dating four women during the same period of time, but perhaps you were not intimate with more than two of them at the same time. I don’t remember the details.
Kudos to her for being honest and not hiding her lifestyle just to get what she wanted.
And Kudos to you for not your values just to get what you wanted.
Be well.
Comment by Cathouse Teri
| August 7th, 2008
There is not a man alive who thinks about sex more than I do.
Comment by dadshouse
| August 7th, 2008
Lance - I respect that you respect me. (Haha - that sounds funny. It’s a male bonding thing, I suppose). Like I said, I have friends who have multiple lovers, and I don’t think less of them. It’s just not my thing. I really would like to break totally free from physically-based relationships (i.e. booty call partners) and enter something with more emotional depth. I’ve been in committed relationships post-divorce, and they are indeed more fulfilling. But in the meantime, booty meets some needs.
Someone pointed out that I probably would have taken this women to Napa and slept with her anyway, whether I thought there was long term potential or not. That’s true!
Mama LLama - yes, I wrote a post How to Date Four Women at Once. But that was about having an on-call pool of companions and activity partners. I was only intimate with one of them.
Teri - I don’t doubt your sexual openness and desire, but I’ll call you on that one. Men think about sex A LOT. Now multiply that by a zillion and you get a better picture. Sometimes it’s a fleeting “I’d sleep with her” when a woman walks by. Sometimes it’s way more explicit. But it’s a recurring theme that buzzes around in a lot of guys heads.
Comment by Cathouse Teri
| August 7th, 2008
This ain’t news to me. My statement stands. :)
Comment by justrun
| August 7th, 2008
Well, this is a world I know almost nothing about. I know men think about all this way more than I ever could, but it’s interesting to me how the tables turned.
Anyway, that’s only like half a comment, sorry. I’m going to be fired for reading a post about sex at work though, so we’re even. :)
Comment by Jeff Mac
| August 7th, 2008
Yeah, I’m with you, dadshouse. While I’ve always respected the free-spiritedness of the polyamorous folks, it ain’t me.
I’m reminded of a female friend of mine who went out on a date with a polyamorous dude who, on their FIRST date, gave her a book entitled “The Ethical Slut.” Now THAT, my friends, is a free spirit.
Comment by katherine.
| August 7th, 2008
amazes me what generates such extensive commenting…neither Benita the latina’s lifestyle…nor Dad’s inviation and reaction are unusal in the 40 something dating world?
At times the third date expectation starts to feel like a rule…and I squirm when rules are imposed on my “dating life”. While I know there are times when “booty” is the priority…if either partner is looking for exclusivity…I would hope they would bring it up before the breakfast after….
Although…I was sorta sorry for our intrepid hero…
Comment by Cathouse Teri
| August 7th, 2008
I never feel sorry for a man who has accomplished getting laid.
Comment by dadshouse
| August 7th, 2008
Teri - regarding your constant sexual thoughts, you go girl! Whatever you’re eating, pass it around!
Justrun - way to take one for the team. I’m flattered. Do you need a referral for your next gig?
Jeff Mac - here in the Bay Area, it seems it’s the women who are polyamorous, mainly because they can be. The ratio of single women to single men in Silicon Valley is something totally out of whack. I’ve heard 1-to-6, but it’s probably not quite that bad. Still, with more men for women, women can make their own rules, for sure. (On the other hand, I’ve heard in Marin, there are more divorced women than divorced men - so there the men make the rules. Kat Wilder can clarify that one)
Katherine - I’ve learned it pays to be direct and aggressive and confident when it comes to courting and seducing women. Then again, maybe that’s why I seem to find booty but haven’t found a committed relationship in a while.
Comment by Mike
| August 7th, 2008
Liked the story very much and reminded me of when I was a single dad on the dating scene. I applaud you for standing for what your looking for. Miscommunication is always going to happen.
I do have to say dating in my 40’s was a hell of a lot more fun than it was in my 20’s. Mature women know what they want and aren’t afraid of going for it. Keep plugging away (sort of speaking)and you’ll find the one. I did after a few years and more ladies than I will ever admit.
PS I did it down here in So Cal.
Comment by katherine.
| August 7th, 2008
direct, confident, and agressive should work for both “booty” (I am hatin’ this term) and a committed relationship…depending on what your goal truly is.
I’m thinking your efforts to court and those to seduce produce far differnt results ?
Comment by dadshouse
| August 7th, 2008
Mike - glad to hear there’s hope in my 40s!
Katherine - sorry if booty is a term you dislike. It really just means “casual sex”. I happen to prefer longterm booty call partners (ie. lovers) to one night stands. I don’t call them friends with benefits if we don’t do anything else!
I think in my earlier comment, I might have placed too much blame on Silicon Valley. Polyamory happens everywhere. Benita didn’t live in the Valley, she’s in the city. I think years of dating frustrations in Silicon Valley have resulted in me chasing more casual than serious relationships.
My direct approach has worked for both serious and casual relationships. I simply happen to be meeting (or attracting through my choices and actions) women who want casual rather than serious relationships right now. Perhaps I need to correct my course and align it with what I truly want, whatever that is!
Comment by whatmenthink
| August 8th, 2008
Wow! That story was HOT David! Brazilian women are very sexy.
It could have been worse! What if you found this out before your playful romp in the sheets? At least you have another booty call.
Comment by mad cartoonist
| August 8th, 2008
Oh, that’s sad.
But I guess it’s just another reminder for all of us to TALK TO those we are enamored with, not just assume (or “project our hopes onto them” as one poster above totally nailed it).
I’ve had the same problem…why do I tend to mentally picture a rosy and improbably perfect future with a man I’ve just started dating & hardly know?? Maybe a joke on the human psyche by those pesky and fun hormones?
On the other hand…I loved your “indecent proposal”! I’d go for it! You must try that again…
Comment by Lance
| August 8th, 2008
@Teri: Getting laid isn’t an accomplishment, it’s a basic need, like in Maslow. This is part of the problem.
Comment by poetreearborist
| August 10th, 2008
I would have slept with you on the second date too. And the third. I like this woman. She says what she wants without worrying if it’s the right thing to say. She is being honest with you, and honest with herself. You want different things at this time in your lives. Currently, my best advice nugget would be not to allow this to turn into an infatuation. It certainly has the potential for it.
Comment by QTMama
| August 11th, 2008
Third Date is when the sex comes? REALLY?
Damn. I hope he didn’t think that. ;)
And onto the other parts of the post … if it’s her culture to have multiple lovers, ok so be it. But if you want her all to yourself, it’s completely fair too. And sadly, there isn’t much room for compromise here. *hugs*
Comment by Relationships-Sex
| August 11th, 2008
David, this is the first time that I have come across your website and I really enjoyed reading this story…so much of it rings true after having lived in San Francisco many years. The idea of girls who embrace sexual freedom is much better than girls who actually embrace sexual freedom…especially if you really like them.
I had a similar experience with a great girl from Chicago. Here’s that story entitled One Thing a Woman Should Never Divulge: http://www.thisishowyoudoit.com/blog/women-should-not-say/
Keep up the great posts! Take care,
Richard
Comment by Susan
| August 12th, 2008
I have to say I’m kind of bummed reading that, and the way it turned out for you, being a singularly focused, longer-term minded kind of gal. Apparently I didn’t get the memo!
(Although I’m not Brazilian, don’t have a brazilian, and don’t live in the Valley, so I guess I’m ok. Or just lame ;) )
Comment by supermom
| August 14th, 2008
Such an innocent girl I am. I didn’t know date 3 was ‘the’ date.
Sorry it worked out the way it did.
Comment by organizizer
| August 19th, 2008
“I didn’t expect anything, but had we at some point both chosen to date exclusively, then I’d prefer she only slept with me.”
I thought you said she clearly told you – as soon as you asked – that she would not choose to date exclusively. Sounds as if you wanted someone to sleep only with you, no matter what they had agreed to.
The contradictions in your words make my head spin. You claim you didn’t expect anything, but paint an excruciatingly clear picture of disappointed expectations. Makes me wonder: Are you being entirely honest with yourself?
If you do not bring up the things that are important to you, then *you* - and you alone – are responsible for your lack of knowledge (and whatever expectations you project into that void).
It never ceases to amaze me, the sheer volume of important things Americans assume, instead of talking about. And I was born here!
Comment by dadshouse
| August 19th, 2008
Expectations and preference are two different things. Not sure why your head is spinning. Hope it doesn’t fly off.