Bitter, single woman? A first question is why is she bitter? Once this question is answered, advice can be offered. However, is 'bitter, single woman' requesting advice? If she is bitter because she feels she is unsuccessful with her intimate relationships, asking her why she feels she is unsuccessful is a good starting point.
She may already know why she is holding onto bitterness and having her disclose her thoughts will help her communicate more clearly to herself and reduce confusion. Has she identified a trait or set of traits that causes her to ruin her relationships? Perhaps she does not listen well, is bossy, she runs away from discomfort quickly and easily, chooses people with problems they do not intend to resolve, is confused, not clear with her boundaries, operates from an fantasy or idea of what a relationship should be, recognizes only her wants and needs, does not know how to work with others to identify and achieve common goals, is out of touch with her feelings, is impatient, is unable to recognize kindness, is unable to commit, does not know how to speak graciously, has a drinking or substance-abuse problem, does not know how to take responsibility for her attitudes and actions, has a strong fear of intimacy, is confused about her sexual orientation, does not know how to establish and maintain friendships, is impulsive, discloses too much about herself, does not know how to maintain confidentiality, is an emotional drain on others because of neediness or excessive communication, is off medication that she was instructed to take, is not taking the correct medication doses nor on time, does not have time for relationships but tries to have them anyway, does not know what she wants in a relationship, doesn't know what to do with her life, is holding on to resentments from the past, does not know how to express anger is ways that are generally acceptable to others, does not know how to identify and express her feelings, is too tired all the time, does not have proper nutrition, is not getting enough sleep or rest, is not taking care of her health, or (fill in the blank).
If she asks for advice, ask her to share what she thinks about her own attitudes and behavior. If she does not know, then ask more questions. Ask her to identify and describe the best relationship she has had. Ask her to explain what she appreciated about that relationship and why she felt it worked for her. Have her tell you why the relationship ended and whether she is still in contact with that person. Then ask her to describe a relationship she would want to have in her life right now. Ask her if she there is anyone in her life right now that she is interested in getting to know better. Ask her to provide some possible plans she can implement to increase self-disclosure to this person. Ask her if she believes that she is bitter. If she says that she is bitter, ask her to describe how she has been hurt. Ask her if she wants to be free from her bitterness. Tell her if she wants to release her bitterness she needs to feel and express her emotional pain. Once she has done that encourage her to move forward letting go of her resentment. If she states that she is unable to release her resentment, reminder her that she may still be holding onto to hurt. Tell her that she needs to be patient with herself and take her time working through loss. Releasing small doses of pain a little at a time and using a journal to record perception, thoughts, impressions, and feelings can be helpful.
During her time on her own (not in an intimate relationship) is a time for her to focus on taking care of herself, being good to herself, fortifying herself, creating pleasant experiences, learning how to take advantage of her present experience to improve her life. Jumping into a new relationship without a strong awareness of self-care can result in significant confusion, frustration, and unhappiness.