I hope you don't reprove me too harshly in your response, because I'm already acutely aware of my tacky behavior. But for a chance at your advice, I'll gladly take whatever you shoot my way.
I've received a lot of help from my undergrad advisor over the years -- several years after I graduated from college, she wrote me recommendations for grad school applications and gave me invaluable advice about the process; she proceeded to publish my work, was a member of my thesis committee, etc., etc.
Horrifyingly, I have never sent her a gift or a formal thank-you note for any of this -- for ALL of this. I have written her grateful emails and have followed up with her to give her news of my progress and ask after her, and I have put my heart into wording my emails so that she understands my sincere gratitude and respect and admiration. When I ask her for help, I always couch it in a way that (probably over-) states my understanding of how busy she is, and my sincere desire for her to say no to my request if she doesn't have time or inclination. She consistently says yes and then some. To disclose further, or maybe just to rationalize, it's true that in her busy-ness she never responded to a few of my friendly emails and was on my committee only in signing her name to a form (literally).
Regardless, for the past six months I've realized with growing shame that I just have to send her a gift as a formal token of my appreciation for her support. I'm now sort-of-gainfully employed and can afford it (though I could have always afforded the price of a stamp). I'm also in a much healthier, more mature and stable frame of mind than I was when I first approached her for advice (I should say that when I applied to grad school I was suffering from untreated bipolar disorder and was not functioning in a lot of basic adult ways, so I didn't even really get that I was voiding a social contract; I now know, and am in treatment, but nevertheless this sort of thing is still a struggle for me -- it can be very difficult still to cross basic things off my to-do list).
The thing is, while I have been thinking about what to send her, not thinking I had a deadline, I decided to apply to further graduate study this fall. A letter from her could really help, but I fear I can't ask her. If I weren't applying I'd have no trouble 'fessing up to my rudeness and sending her a gift with an effusive note. But I don't think it's an option to send a gift after all these years and follow it two weeks later with "ALSO, please do yet ANOTHER time-consuming thing for me!" It would seem so calculated and ingratiating (I say as I calculate how to be ingratiating). And I don't want to ask without having properly thanked her for her previous help, because I'm done with being rude, plus I worry it would be the straw that broke the back of our relationship. Ideally I'd love to just ask her, have her say yes, and then send her a big old bouquet. Alas.
So tell me, please: Can I send a gift, then ask her for a letter? Ask her and send a gift later? Or should I send a gift and ask others for letters, saving myself my guilt and both of us our mentor-mentee relationship? I am trying to figure out whether my will to keep learning and growing in my field should out-chime the klaxons of my shame. Part of me thinks I should even just wait a year to apply (but I'm getting old).
Help! and thanks. You'll be receiving my gift soon.
Dear Helplessly Indebted,
Send her a gift and tell her what you told me. Tell her, sheepishly if you must, that you'll be soon asking her for yet another favor in your seemingly endless stream of requests. Just tell her. Your honesty about your feeling of indebtedness, as well as your success in facing your own problems, cannot but be touching. It may feel awkward, but it can be handled with grace if you are just as honest with her as you have been with me.
Also tell her this: Now that she has helped you in so many ways to gain a foothold in the academic world, if there is any way you can be of help to her in the future, any way at all, personal or professional, you stand ready, nay eager, to leap into the fray.
Then you have acquitted yourself well, discharged your obligations, and placed yourself at her future service. But you must act. It is not enough to simply be willing. If you see an opportunity to do something for her, do not wait for her to ask. Just do it.