I’m not sure I want to date again

We'll be taking a two-week chat break and then back the week of the 8th. But send me notes and letters, etc. And chime in for podcast, Season 3.

Dear Meredith,

I just turned 49 this month. The last man I seriously dated was in my youth. We were deeply in love. Then I got pregnant, so we decided that the right thing to do at that time was to get married. My daughter's father and I had everything planned. We had a priest, venue, date, my dress, we were both excited about the baby, and then he began to have doubts. He wasn't sure about us anymore. I was so heartbroken, especially when I found out he was seeing someone else. It took me years to heal. Being a single mother was not in my plans. I was in medical school and the only one of my siblings to go to college. Everything changed and my heart hardened along the way. I like to say that the reason I never seriously dated anyone was because I didn't want to risk bringing the wrong man around my daughter, but I think I was more afraid of being hurt again.

The man I am currently dating is 45. We met about five years ago at a coffee shop. Out of impulse I suggested to a stranger to try the coffee from my country because it is the best. We talked, exchanged numbers, and started to see each other frequently. But it is a strange relationship because I never feel like he reciprocates the same feelings. He rarely calls me, and we see each other every two weeks, if I am lucky. He is always busy. When we are together everything is wonderful but when we are apart, I feel forgotten. I have expressed this to him. We have been on and off since we met. I am the one to call things off when I get tired of his lack of communication and presence, then he appears again to try to make things work but goes back to being the same.

The longest we've been apart was two years, and during those two years I met another man online from another state. We would message and call each other quite often. We shared the same values. We met for the first time this past winter, while I was on vacation, and had two wonderful dates, but after I came back home, I stopped hearing from him, so I decided to cut off communication. Then in April the man I am currently seeing came back to my life, but I don't know how long this will last. I am not sure if the reason I am seeing him is because I am afraid to be alone. He makes plans only when he is available, and it is usually at the last minute. He has expressed that he loves me, but something feels off. I'm not sure if after this relationship ends, I want to attempt at dating again. My daughter moves out next month and I feel like I haven't done anything in life but provide for her. She says I should have focused on myself a long time ago. Now, with her leaving, I don't know what to do on my own.

– Hopeless at love


I see two very hopeful points in your letter. The first is that you are capable of meeting people. I mean ... you picked up someone in a coffee shop. That's difficult to pull off (unless you are in a romantic comedy), and you made it happen. Then you met someone online and had enough of a connection to meet up with him in person. You did all of this while working and raising a child. Imagine what connections you might make with more time for yourself.

The second hopeful thing is that you want to be someone's partner. You desire more phone calls and quality time. You're looking for shared stories and plans for the future. You seem capable of letting someone in, which is a great place to start.

I imagine it's very stressful to think about adjusting to life without your daughter in the house. Please know that you don't have to make any monumental decisions as you prepare for her to go. There's no need to shout "I'll never date again!" from the rooftops. It's better to focus on making room in your life for what you want. That means breaking up with this long-term boyfriend. That's what you want to do, right?

You write of the end of your relationship as a when, not an if. Knowing that, you might as well get it over with and cut ties. Then think about how you'd like to spend your free time. It doesn't have to be all about romance. You can put more energy into making and spending time with friends.

Give yourself the opportunity to get to know yourself all over again. If you spend time on yourself, you'll get better at knowing what you might be looking for in someone else.

– Meredith

Readers? Time to break up?