here's how your role model (ME) did it in 8th grade
STEP 1. Obtain woman (or in this case, woman-in-training)
STEP 2. Take that bitch on a bike ride, go around town (bonus points for pool)
STEP 3. Take her out for lunch on the bike trip, go to some local restaurant or fast food joint (none of that olive garden stuff)
Step 4. Women love a man whose in tune with his outdoor side, go to the park and go venturing with her (and maybe a picnic!)
Step 5. Take that bitch home, date successful
As for the asking her our part, just do it you friend