A painless breakup?

I’ve been in an “on again/off again” relationship for the past seven years. I was considering marriage until I ran into the woman who was my first love. We broke up because I moved here to attend college, but she has been on my mind for the past 11 years. After meeting again, we spent a week together in Los Angeles, keeping our relations strictly non-physical. The feelings are still there between us and she said that she wants to pursue a relationship. I am still involved with my girlfriend. In my heart, I want to pursue a relationship with my former girlfriend because I’ve been through so many ups and downs with my current girlfriend. How can I share my feelings honestly with my current girlfriend without hurting her feelings?

That’s an excellent question. The best time to ask it was before you decided to spend a week with your former girlfriend. It wouldn’t guarantee your current girlfriend’s freedom from hurt. It’s likely that she would feel some pain at the close of a long-term relationship, even one that has been ruptured and repaired so often. By telling her that you wanted to spend time with a woman that you were interested in romantically, you would have saved her from the betrayal of your emotional affair in Los Angeles. That reminds me: did you ever tell your current girlfriend that, for the last 11 years, you’ve been renting out a portion of your mind and heart to a former girlfriend? Perhaps some of your current relationship’s volatility was created by your inability to fully commit to the present because of your emotional investment in the past.

Only you know whether either woman is your life-mate. Once you find such a person, know that you can sustain mutuality by continually cleaning the internal filters that keep you from being honest. That will allow you to tell the truth with tact and kindness in the moment so you can avoid struggles like your current one: a sudden desire for honesty fighting against years of lies to yourself.

After a long flirtation, I became intimate with a man 11 years my senior (I am 23, he is 34). The age isn’t so much what throws me, but more that he has a 7-year-old daughter and is a widower. I am normally very cynical when it comes to dating and love, but I feel as if there is real potential here. Here’s my question: How can I best express my interest and care and continue what we’ve started without intruding on his family? Which boundaries should I stay mindful of and which am I able to transgress?

Your friend’s daughter is old enough to worry about dad’s affection’s straying too far from home. So while it’s possible that you might be a welcome source of grrrl power, you may also be seen as a threat. If she doesn’t seem to like you, it’s not personal, it’s protection. Let her have her feelings and don’t try to be anything other than dad’s friend. Be friendly, genuinely and consistently interested in her and extremely patient. It’s also important not to shape your behavior according to stories you hear about the woman who died. Remember, sainthood is traditionally granted after death. I suggest that you focus on opening your own boundaries of cynicism so that you can give and receive love freely. You may have had sex with this man, but your struggle to learn how to be truly intimate with him has just begun.