Dear Neil: I’m 28, and I fell in love with a 42-year-old woman. She broke up with me after 6 months, saying it’s not healthy for a woman her age to be having a relationship with a man my age. I’m not agreeing with her reasons to break up, and I know she loves me. Can I wait this out and win her love back?

Hopefully Trying

Dear Hopeful: Likely not. It sounds that she is saying that she doesn’t think this is a good long-term fit for her, and she may have a host of reasons other than the age difference that she mentioned. But you could request an extremely honest conversation with her about her reasons, and see if any of them could reasonably be worked out or resolved. But don’t hold your breath. A woman who says no to a relationship very likely means no, and you are unlikely to change her mind.

Dear Neil: I have been in a year-and-a-half relationship with a good man, who helps around the house and is good to my children. But I’m not into him like I used to be. I feel really bad leaving him, but my happiness is more important. What do I say to end this relationship without hurting him?

Wanting Something Else in Phoenix, Arizona

Dear Wanting: If this man has given you his heart, there is absolutely no way of breaking up with him that won’t hurt him. There is simply no way around the fact that it hurts to be rejected by someone you care about and want. But you could be sensitive and compassionate when you tell him. It won’t make him feel any better, but it honors the sweet and/or loving times the two of you shared together.

Dear Neil: This girl gets on the train at the same stop as I do, and gets off at the same stop as I do as well. I want to ask her her name and number, but I’m scared to. Can you suggest a way for me to get her attention?

Scared in Singapore

Dear Singapore: All men (and a variety of women) face this same predicament. How do you start up a conversation and express interest in a stranger without feeling awkward and foolish, and without risking rejection? You are doing something that requires risk, and this kind of risk can feel very scary.

But not risking is even worse, because then you are guaranteeing that you won’t succeed. In essence, you are rejecting yourself because you’re fearful the lady will, so you’re not even giving yourself (or her) a chance.

Here are a few ways you could break the ice: (The direct way): “You interest me. Could I invite you to lunch (or for a drink)?” (The less direct way): “I see you on the train a lot. My name is Harry. What is your name?” (The indirect way): “We board the train at the same stop. We must live near each other. My name is Harry.”

Whatever you do, remember the saying: “Carpe diem.” Seize the moment. If you don’t, some other guy will.

Tagged: breaking up   rejection  

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