Great question!
Speaking for myself:
On your basic question of regret for not approaching men I find attractive - never. I don't do initial approaches.
Not being bold enough and honest enough to express and act on my true level of interest in a man once we were seeing eachother, out of fear he could not handle it and run - once. How I dealt with it? I realized that he was the only regret I had - that I had witheld my love out of fear. I have never regretted
giving it, though. There are no question marks left when I have
given my love well. Since then, I know it is a betrayal of my self and a form of dishonesty for me to not love honestly.
On a larger life scale: I almost died from a serious illness 5 years ago. When I realized I would most likely die, I had peace. I realized I had no regret - no loose ends - no apologies I needed to make - noone I love who doesn't know it. (of course I didn't want to leave my children - but I had no regrets to contend with in my life itself. But I do not perceive money, education, career as my life - I look at my realtionships - my "love" lessons - as my definitions of a life well lived. All the other stuff is just stagesetting but it is the actors/players/people that are what matter.)
I think it is because I strive to not stay bound to suffer the pain of the past lessons to repeat over and over again. Glean the lessons of loving well and move forward - that is what we are here for, I believe. The emotional experience of remorse in wishing I had known/done better is not enough - nor is a compassionate response for self enough (and I digress but want to add that there is a danger line there because I can slip into self-pity if I am not mindful of my process - so by compassion I do not mean pity). Moving forward and not repeating the same error is what releases/frees me from the bond of regret.
I have this little pic under the glass top of my desk:
http://imgs.inkfrog.com/pix/Hazel/0637T.jpg
I called a friend of mine last night about this question of yours - I have known her over 20 years.
She has been struggling with regret lately - although I did not recognize it as "regret" as I have been processing her path with her. (I did identify her inability to move forward in her life and not be bound by her past, but the verbage of "regret" spurred on by your question is very helpful. She knows about my experience of reflection regarding regret when I was ill. It is not uncommon for us to call eachother up and dive right in to the heart of a matter without exchanging niceties.
I will call her "Mary" below, and share the part of how it went with you...
LL: Hey Mary - I want to ask you something - how have you dealt with regret in your life?
Mary: (laughs) Not as well as you, Lovely, that's for sure .... (serious tone with some shame around the edges) I don't think I've dealt with my regret well at all.
LL: What do you regret?
Mary: (Contemplative) Well, I have failed to order the life that I want for myself.
LL: How do you deal with that fact?
Mary: Well, I confide in... well, dear friends like you. I verbally vent about the outcomes of situations and how powerless I feel. You know, I think a lot about those quotes you wrote down for me that one day from
White Oleander - about responsibilty for my choices and how I need to remember the truth of who I am... that helps me gain perspective.
(She is referring to a recent conversation where I sited these quotes from the book:
"Oleander time," she said. "Lovers who kill each other now will blame it on the wind." and
"We received our coloring from Norsemen. Hairy savages who hacked their gods to pieces and hung the flesh from trees. We are the ones who sacked Rome. Fear only feeble old age and death in bed. Don't forget who you are." )
You know, how you talk about ignoring the preconceived notions about the way you THINK you are - the things you SHOULD have done and simply deal with the truth of who you are in the moment and draw strength and comfort in that. To not be a coward in my life today.
You know, also, its like in the Bhagavad Gita, where Rjuna is going to war. On the "enemy" side of the people he is supposed to kill are his revered teachers that have helped him reach this point of being a Warrior. He is conflicted.
Lord Krishna says something along the lines of "There is no way you can unentangle from the events that have led you to this place".
LL: Yeah... kind of like "when you see the Buddha on the road - kill him" (both laugh) Yeah - the Student surpasses the Master. (more laughter)
...
So, I have learned I must have a willingness to change, to be flexible - to allow my life to move beyond the lesson that the feeling of regret alarms me to notice- beyond the teacher - to "hack the gods to pieces and hang the flesh from trees". To let the old ways that have not served me well go. - And to to be willing to move beyond what used to serve my growth - but no longer does.
Kind of like Pharoah in the 10 commandments : "So let it be written - so let it be done" LOL
.. additionall thoughts: Sometimes we have a plan for our lives to go one place - and life takes us somewhere else entirely - to trust the rhythm of the journey is important. To remember it is a soul journey teaching us to love courageously. Manifested and teaching us in the physical realm of going after what you want for your life - whether a phone number or whatever.
Regret is just an emotional warning sign we are not living in harmony with our truest self/highest path. IMO