Edit: I've cross-posted this on AskSeddit. Should it have gone there in the first place?

Some of you may have read my recent FR. Quick context: I'm a 23-year old virgin who's making slow progress in game, and my current major sticking point is sexualizing contexts and escalating kino. It always feels very unnatural and forced to me, which I'm sure is perceived as un-suave and freaky by the female. Until I can get an intuitive sense for what to do and when to do it, I don't think I can get over this sticking point.

Both the abridged and full versions of Dicarlo's Escalation Ladder on the side bar have been helpful. (By the way, while the abridged outline is good, I recommend also reading the full version, as it provides far greater detail.) I'm fine with the "Incidental Class 1" kino (e.g. shaking hands, tapping on shoulder, touching to emphasize points, high five), but I'm really having trouble seeing how the "Overt Class 1" kino is initiated (e.g. holding hands, arm-in-arm escorting) - do you just start holding her hand? Logistically, I just don't see how it happens so that it appears natural.

Compound this with my current "headache," a possible grocery shopping trip with a HB9 this weekend. I am a mentor to four people in a non-profit educational organization, and I'm really into one of them, the HB9. Up until now, we've had a group dinner, and HB9 and I have been texting back and forth occasionally, but given our respective positions, the relationship has thus far been strictly professional. Given any opportunity, I make sure I come off as fun and sometimes random/spontaneous, but it's been difficult not to come off as a predator feeding off a vulnerable protégé. There has been zero sexualization thus far, and also no kino whatsoever. The best I've been able to do is, when she commented on a long day, say, "The best things in life are long. Take spaghetti for example!" (Felt inappropriate and off-putting to sexualize, so I tried for cute.)

We have a lot in common. I'll spare you the details. Basically she mentioned that she really likes grocery shopping, because it's a big stress reliever. I know that this week will have been very stressful for her, so this Friday evening, I plan to text her and say, "I'm going grocery shopping tomorrow. You should come with." (This single text message has undergone at least 5 revisions after reading a bunch on text game and asking friends.)

I estimate an 80% chance that she will respond favorably. Let's assume we go on our little shopping adventure. Now we're back at my kino & sexualization problem. Put my sticking point together with this current professional situation, and I'm completely lost. (By the way, in our respective professional positions of the organization, it is not "outlawed" to be dating or in a relationship.)

I would love some help from you experts out there. I think I need a list of canned actions. Maybe things like:

  • When she grabs some cabbage, accidentally...
  • When she looks at a box label, step...
  • When she gets close to the cart, lean...

or whatever. In time, this will probably get more intuitive, but until then, I just need some smooth ideas. Oh and although I love meat references, they won't apply since we're both vegetarian. :)

THANKS GUYS! I LOVE YOU.