Why didn’t it work?

I can't chat today because I'll be out of the office planning a Love Letters event, which you will hear about very soon. I promise I'll make it up to you.

I just wanted to pick your brain about a situation I had last year. I am a man in my late 20s, and I met a girl (same age) last year who I dated for about 4 months. It obviously wasn't that serious, but for some reason the lost potential still bothers me.

We met on an online dating site and things started off really well. However, after a few dates, I started getting vibes that she was already ready to be in a relationship with me, which freaked me out a little bit. I'm pretty selective about who I date, and although I liked her, I didn't want to rush things and I didn't want to give her the wrong impression so I pulled back a bit. But then as I got to know her, I realized that this is just her personality -- she's an extreme extrovert who gets excited and wears her heart on her sleeve while I am more reserved and don't always show a lot of emotion. Regardless, we continued dating, and I began to see that she really was an awesome person. I started developing feelings for her and I was beginning to think that there could actually be some long-term potential.

I don't fall for too many girls like that, and it had been years since I had felt that way about anyone. But there was one thing that was a little frustrating/weird to me -- she was never available to hang out on weekends. She grew up in another state and went to college in a different state, so a lot of her friends live elsewhere, and she would make plans for weekend visits weeks/months in advance. I would ask her early or mid-week what her plans were for the weekend, and it was always the same answer -- she already had plans. After getting this response a number of times and then having her tell me her weekends were basically booked solid for 3 months, I lost a lot of motivation. I wanted to start making more of an effort, but I felt limited in what I could do, as the only time I could see her was on Sunday nights and one or two other nights during the week, and it got to the point where all we did was sit on the couch, order take-out, watch TV, and go to bed. As I looked back on it after things ended, I realized we had never gone out together on a Saturday night, and she never had the chance to meet any of my friends, which I think is an important part of getting to know someone.

I was pretty baffled when she broke things off, saying that things weren't progressing and that she had lost the feelings she once had because of my seeming lack of interest/effort, and that the push-back she felt from me in the beginning is what made her start to shut down. To be fair, I was not great about calling/texting just to chat between the times we hung out … but part of the reason was that I wasn't ready to do that when all I could get from her was weeknights. I don't need too much in a relationship and I actually like it when a girl has her own friends and a life, but at some point, social lives usually start integrating at least a little bit.

The reason it still bothers me is because we got along well, seemed to have similar values, and we both really liked each other ... just at different times -- her at the beginning and me at the end. I did ultimately let her know how I felt and I (regrettably) pleaded with her to give it another chance to try and make it work, but she was just done. What really killed me was that as she was breaking things off, she told me that on paper I am exactly what she wants, but she didn't think she could get back the feelings she once had. I've been out with a number of girls since all this, had a couple 1-month stints, and have felt some decent connections, but nothing like what I felt with this girl last year, so I'm left with a lot of regrets about the whole thing because I think we could have made things work if we had just communicated better and discussed things sooner.

So here are my questions: Was it normal for me to pull back like that in the beginning when I felt like she was coming on so strong, or should I have embraced it? How often should a guy be calling/texting with a girl during the first few weeks/months when he sees (and sleeps with) her twice a week? Was I wrong in thinking her expectations for relationship progression were unrealistic when we never saw each other on weekends?

– Can't Believe I Am Writing to a Dating Column, Boston

I'm not convinced that this is your fault, CBIWTADC, at least not the stuff that happened at the start of the relationship. We're all a bit weird when we're trying to figure out whether we like someone. You pulled back -- but then you stuck it out and rallied. You wanted more and more of her time and you made that clear. In the end, she broke it off and you pleaded with her to stay.

Of course, it would have been great if you had said, maybe during month two, "I'm starting to feel slighted that you can't see me on weekends -- and I’m desperate to see you on a Saturday night and wake up with you on a Sunday." But she could have asked you to come with her on a weekend trip. And she absolutely could have cancelled plans with friends to spend some time figuring you out. She didn't make you a priority.

And as for the texts, don't even think about them. You wanted to see her in person. That's all that counts. Texts don't make or break a relationship.

I need you to know that you're not as smitten with this woman as you think you are. You liked her a lot, but the relationship had serious flaws, and you were never really satisfied with the way she handled herself. You need someone who makes you feel comfortable, someone who encourages you to be honest. This woman inspired you to feel helpless and passive-aggressive. You've learned a lesson about communication for sure, but I believe that this relationship would have ended no matter what. So let her go and give some of these other women more than just a month of your time.

Readers? Am I right to say that this would have ended no matter what? Or is he just so silent about things that she thought he wasn't interested? Should she have cancelled her weekend plans? Did he fail by distancing himself in the beginning? Is this about everybody wanting what they can’t have? Discuss.

– Meredith