Other than long black eyelashes, the best thing my father gave me was a model for asking for things. Certainly not a perfect model as he has no shame. (Really, he doesn't. Boundaries are in question here, in the nicest sort of way.) It's more of a yardstick along which to compare my own requests on a continuum of how awkward it is to make the request against what the reward will be, while also considering the imposition involved and the relationship itself.
Let me start small. Both of my teen girls are attending a four-week summer program in theatre, dance, and music. We submitted their class choices in May in priority order and when the schedules came two weeks ago both girls were disappointed. Teen didn't get the videography class that she hoped would help her develop a better understanding of what a film major might entail. Also-Teen, the show-stopping singer, didn't get a choral or vocal class. But the information sent with the program was clear that the only changes that would be made were for administrative errors or level placement.
Teen debated whether to say something before the first day of class, weighing the embarrassment of asking for a change that specifically seemed to be outside what would be considered. When it came down to it, we both agreed that five minutes of awkwardness was worth the possibility of four-weeks in the right class. It turned out to be painless, with the administrator making the change quickly and pleasantly. With that knowledge - along with realizing that Also-Teen was definitely in a dance class too advanced for her - the girls went back to change her schedule to get a chorus class. Which they did. Perfect.
In that case, the girls weren't asking for anything extra. The asking was simply going against the implied procedure and the old standby of "you get what you get and you don't get upset." It's harder when it involves a true favor that puts someone out for your benefit. I have this situation coming up where I'll be staying with my mom for a week in Baltimore for her treatment, and need some help getting the girls home from their summer program. Here I have to weigh the asking against the awkwardness of asking, but also along the relationships I've made and the imposition it would cause. I hate this kind of asking, but have made it easier for myself by generally being the person who says yes to other's requests or offers favors where I see I can help. (Usually in carpooling. It's all about carpooling.) But it's still difficult to ask for help.
Then there's the hardest request of all. The one that relies less on the imposition and more on the relationship itself. My example, coming up soon, is wanting a place to stay in New York City the first full week in August to attend Also-Teen's Broadway program. I wouldn't put someone out by hosting us, but I'd happily accept a week in someone's Manhattan apartment as they vacation or live elsewhere. I've been lucky enough that we've gotten by this way for two years as my cousin was staying in Los Angeles and my friend was staying in Amsterdam. It's a difficult thing to ask - for someone to let you use their home - being so personal, so reliant on trust and the relationship. But in my weighing against reward, it would save me two or three thousand dollars on getting a hotel that was safe, clean, and convenient with two teens. So ask away I will. (Like now. I'm kind of sort of even asking now. You know, if you happen to have a place to lend to a future Broadway star.)
When I think about it over the years - and I have - I've found that there are RULES and there are "rules," in anything from the written directions for a summer program to the social conventions of relationships. I've come to a conclusion that you generally won't get what you want by not asking for it. And yet, it's still hard in considering what you ask for.