Third Time's the...Charm?

For someone so painfully shy, he was painfully persistent.
I could tell he had depth, he was a gentleman, and he was nice. But after a few dates, our conversations remained superficial, long small-talk discussions. Nothing too deep or personal, at least on his part, whether about himself or in asking me questions.
I think I actually gave him a few weeks to open up, to relax. But when I saw that it was going to take much longer (if at all) for him to let his guard down, I thought long and hard before finally making the call one Friday afternoon. (side debate: is it better to break up on a friday and make the other person have to deal with it over the weekend or is it better during the week when work and other things can distract from the pain?)
The following week was Purim. My family and I went out for the seudah and when we came home there was a huge Mishloach Manot basket on the stoop with a stuffed kitten and the most heart-wrenching love letter, asking me to give him another chance. It ended with "I'm waiting for your call."
Now, it had not been easy deciding to end the relationship the first time, now I was forced to reconsider! After doing so, I decided to stick with my original decision. I had a vision of what life with someone so closed could be like and it didn't appeal to me. I called him and broke up with him AGAIN. In my defense, I did it as gently as possible each time!

Just so we're all on the same page, that was breakup #2. As the title suggests, the story does not end here.

A few days letter I answer the door and there he is. With a dozen red roses in his arms. Again asking me for another chance.
I was so stunned, felt so cornered, I said okay. WHAT WOULD YOU DO???? It's one thing to break a heart, it's another to kill a man while he's down!

I really did try hard to keep an open, blank mind that night. He really went all out. We went to a classical music concert, which although boring, was appreciated. We ended the evening with a horse and buggy ride (so sweet! But if I can be super mean here, I'd ditch the buggy and just take the horse). I don't remember if the drive home was akward or the usual light small-talk.

I had a decision to make. And for the THIRD time, I ended it. Sadly I don't remember how I did it that last time, but suffice it to say this time he got the message.

P.S. My sister called me a week later with a confession. Before confessing she made me promise not to be mad at her. NEVER FALL IN THAT TRAP! It was her opinion that I was unsure of my decision and needed some nudging. So after Purim and the love letter, she spoke with my father. Who spoke with him and encouraged him to try again.

The roses were the guy's idea.