It takes a while to know anyone well enough to give an insightful response. If you give an interpretation too soon it may seen too personal or critical and turn the talker off. I remember what a terrible time it was for me when my parents divorced. I don't want to think about that, so don't say something like that again. After knowing a person well for a long time, one may be able to provide some brilliant insight occasionally.
Great insight is a rare event, however.
Even highly skilled therapists spout profound, creative insights only infrequently. You might suggest that her association of her boyfriends with her father and rejection may make intimacy especially scary to her. If she agrees and decides to select a different kind of boyfriend or to recognize that this is an irrational association which she can deal with, you may have given a 5.0 empathy response.