Contingency plan: office philandering

[Marty]

So I am focusing mainly on cold approach these days, as I have gotten myself into so many sticky messes in the business environment in the past. However, I'd hate to pass up a nice opportunity in the office if there is one.

Specifically, there is a young (25-ish) woman - blond, petite, let's call her Chloe for today - in another division, which means she works in the same building but I don't see her in the actual offices, only occasionally in the corridor or elevator. On the first such occasion when we were otherwise alone, I introduced myself with studied casualness, a sort of exaggerated nonchalance. Something similar to the "detached curiosity" that Chase writes about. This elicited an apparently warm response, confirmed by positive body language at a later chance encounter.

So for my next unexpected meeting, I have the following up my sleeve. Chloe's words are necessarily fictitious, I've no idea what she'll say:

Marty: Oh hey Chloe, I was wondering when I'd see you next!

Chloe: Hello... Why's that?

Marty: I wanted to tell you ... I think you're really beautiful.

Chloe: oh my goodness... Thanks

Marty: -and I'd like to get to know you better. How about a cup of tea some time... OUTSIDE the office?

Chloe: Oh! Well! I guess... You know, I actually have a boyfriend

Marty: Yeah, I know, I think I overheard you talking about him once in the elevator, when you were telling someone about your vacation. Sure, you have a boyfriend, big deal. I have a wife. It's just a cup of tea... You can leave after twenty, thirty minutes if you want to. Will you think about it for me?

Chloe: Oh! Well, sure...

Marty: Great, I'll email you. Enjoy the rest of your day!

Chloe: Okay! You too!

So what's the verdict, gents? Think it might work?

 

[mkivtt]

Err..... I don't really know how to break it to you, but that is totally creepy and totally fail. If it's that obvious for someone who really needs to work a lot on his game (i.e. me), that means it's pretty darn bad. No offense of course, you're here to learn to get better. Things I see wrong:

1. "I was wondering when I'd see you next"

--> Creepy stalker.

2. Calling her beautiful.

--> Immediately puts you in the fawning, drooling AFC category. If you have to complement her, say something like "hey, I like how your earrings/fingernail polish/shoes/armbands match your <insert random stuff>. Very stylish." Or something like that. Maybe "Wow, after dealing with the troglodyte nerds in my department it's a breath of fresh air talking to someone witty and fun *wink wink confident playful grin."

3. Asking her out on an obvious date without any kind of set up, especially right after calling her beautiful.

--> Creepy stalker. Get ready for a trip to HR and possible pink slip if she doesn't like your advances.

4. I know you have a BF.

--> Most girls will not consider leaving their BF and all the invested time, unless you have done a VERY good job of building rapport and so totally more awesome than he is, that it's worth the hassle. The "Oh, I have a wife *wink* *laugh*" line is a good one, it is playful, but I would ONLY use it in combination with what I wrote below: ask her for a casual lunch or coffee, just as colleagues, with NO obvious other intentions, and she says "no I have a BF." THEN you can say "hey, I have a wife! No problem *laugh*. It's just lunch /coffee, nothing more."

5. "Will you think about if for me"

--> Needy, AFC loser behavior.


Here's what I would do. I work in a big company too... and there are a lot of beautiful young women. Talk to her when you see her. Don't stalk her but try to "be around" the water cooler, get a friend to msg you when she is heading to another room or building, etc. When you bump into her, just have some random chit chat. Be funny. Small talk. Laugh about your boss/colleague/the IT department/how bad the cafetaria is/whatever. Just engage her and show her you're funny and clever. NO sexual innuendo or advances. Try to time this around lunch, and say "Hey, it's almost 12. What do you say we get some lunch?" Totally casual and, because you are asking on a high note while "randomly" talking to her, non-threatening. She can perceive it as just lunch for colleagues. Or if it's not lunch time, say you're headed to the cafetaria or break area for some coffee, but it's great chatting, and she should join you.

I wouldn't talk about ANYTHING but random chit chat during that lunch. If it's fun, see if you can bump into her some more, maybe msg her, hang out around the office a bit. Show you are a much better guy than her BF without ever hitting on her. Eventually she will come to see that and you can put a move on her. Hang out w her friends and show them you are better value, so they start talking to her about how she should hook up w you instead. But you need to really time it really right, and this isn't really beginner stuff.

 

[Marty]

mkivtt:

I owe you one big-ass beer!

Seriously, I had this routine all wound up and ready to roll when I saw "Chloe" next... thank goodness you replied to my post before that happened!

Quite right not to sugar-coat it, I totally appreciate your devastating feedback You've done me a favor by being completely blunt on this forum, else it would've happened in real life, and "creepy, needy, fawning, drooling stalker" are words I never want to hear associated with me in the outside world: but shoot me full of holes on this site, by all means.

OMG, does it really sound fawning to say she's beautiful? I planned to say it with easy confidence, of course, as befits my age, status and carefree personality, not blurt it out like a 20-year-old nice-guy bag of nerves.

I think what I'm having trouble understanding, in all honesty, is how to tread the line between the following:

(a) Going "direct" ASAP to distinguish myself from other men who are too much in awe of attractive women to do so, show my interest openly, avoid tiptoeing around my intentions and thus demonstrating confidence, status and unconcern for others' opinions;

(b) Kissing up by overloading compliments and coming across as fawning.

I will have to figure that out. Also, I am going to see if there is anything on the Girls Chase site regarding "neediness". I've read maybe 200 articles but I don't recall one directly dealing with that subject. In reality, of course, I am not needy, if I understand the word correctly; I just don't want to rest on my laurels and I believe I should continually work to hone my skills with women. I have seen too many men, and women, unexpectedly tossed onto the relationship scrap-heap because they have failed to maintain the skill-set needed to find new potential romantic partners, believing that they would never need it again.

Regarding your advice, I don't want to get other people involved beyond what is necessary and I am certainly not going to ask a buddy to SMS me, that really is literally stalking, if word got out then I am beyond the age where that sort of thing could be laughed off as high jinks. I think I might try to play it similar to the setup with "Paula", i.e. get "Chloe" talking and let her do all the work, then break off, implying I'm not accustomed to standing around idly chatting in the office, and suggesting we continue off the premises some day. I want to get it out of professional territory, openly, as soon as I can because I never want to surprise a girl who thought she was just having a business lunch with a colleague. Also I want to protect her reputation (and mine) and get everything away from prying office-gossip eyes and out into the inhibition-dissipating sunshine.

As for your suggestion on hanging out with her friends, that does spark off a few ideas. Again, literally "hanging out" idly about the office with people at her (lower) level could be perceived as tryhard and status-diminishing, BUT as it happens there is a woman who works with her in a very similar role, reports to the same boss, and sits right opposite her, let's call her "Letitia". For one reason or another I got talking with Letitia around the parking deck, and she seemed to show interest so I teased and prodded her a bit, which she clearly enjoyed (but she's a lot less attractive than Chloe). A few days later I took Letitia to lunch (outside the office) and was toying with the idea of trying to have an affair with her (she's married) but I haven't quite decided, I might play it platonic as I'm not wildly attracted.

Anyway, mkivtt, do you think I can leverage that connection with Letitia to get closer to Chloe? For all I know they hate/envy/despise each other as so often happens in women's occupational relations, but I don't know. I am on very good terms with their mutual boss, as I gave him sound advice on a pressing business issue recently, though I'm not sure I want to attempt to utilize that... it feels "beta" to me.

Thanks again, mkivtt, you seem to be a very valuable sounding-board. I'm glad you came to my aid!

 

[Marty]

PS just to clarify, I never said I had any interest in her leaving her boyfriend, I'm just not that sort of guy. On the contrary, I want all ongoing relationships to remain intact; the only aim I have in mind is her - and my - immediate gratification.

 

[mkivtt]

Hmm, since you are on good terms with this Leticia, you could definitely use that. Women love A) men that attract other women and B) men who seems cool, in control, and alpha.

I would definitely go chat with Leticia whenever you see her. If she and Chloe are on good terms, she might share how she ran into this cool guy. Be sure to talk to her it in a calm, natural way that looks like you act like that all the time, instead of hitting on her too directly... otherwise, if she does share that too, then when you do target Chloe a bit later, she may think "oh so he's asking out all the girls and trying to get in anyone's pants..." -->creep. But if you just flirt with Leticia in a cool way, she may just tell Chloe you are fun and cool, upping your value. Then you've already established rapport and piqued interest on Chloe's part when you bump into her.

You could also go see Leticia a few times at her desk later. Help her out with something, be strong and cool, and flirt it up. Then just smile and leave. They're sure to talk about you after you left the room or at the very least it will make you look attractive and confident in Chloe's eyes making it that much easier to talk to her later.

Good luck man.

 

[Marty]

Thanks mkivtt, this makes a lot of sense.

Yeah, I've played it pretty smooth with Leticia so far, so now's the time to reap that dividend if I can. What you wrote actually made me realize that maybe this is what got Chloe's interest in the first place. I had no idea they knew each other... I'd already been to lunch with Letitia a week or more before I first saw Chloe and impulsively made the casual introduction I described earlier. Later, when helping out their boss, I figured that they sat next to each other. It may be that Chloe's warm reception was partly influenced by hearing about me from Leticia... no idea.

With all this discussion I'm starting to catch myself actually thinking of the girls by those pseudonyms; I'm gonna have to be careful not to say "hey Chloe!" next time I see her! That would be tough to dig myself out of