Wait, was she flirting with me? My history shows I’m clueless

She’s one of the managers at a restaurant where I sometimes go for lunch. I’ve been going in there for a couple of years and I know Anna well enough to be friendly when we see each other. She’s about 28 and her company transferred her here from Colorado about four years ago.

She told me a few weeks ago that she was leaving the company for a job with a local competitor. I told her I was sorry to hear that and that I’d be sorry not to see her anymore. When I was there Thursday, she told me it was her last day.

“I really hate it you’re leaving,” I said. “I hope you like the new job.”

And then my bag of food showed up and I turned to leave, saying, “Bye!” It took me a few seconds to realize she was following me out the door. When I realized she was coming after me, I turned to see why — since I was puzzled.

“You understand this is really my last day, right?” she said. I could tell she was flustered but I had no idea why.

“Yeah,” I said with a bit of confusion. “I’m really sorry you’re leaving.”

She seemed exasperated.

“Will you call me sometime?” she said as she thrust a piece of paper at me. She had torn off a piece of a paper bag for to-go orders and written her phone number.

I took it from her, but it was slow to dawn on me what she meant.

“I’ve been waiting for you to ask,” she said. “You talk to me like you’re interested but….”

And then everything made sense. I had been clueless again about what was going on.

— She had been interested for a long time in asking whether I was dating anybody. I thought she was just making friendly conversation.

— When she broke up with a boyfriend about a year ago, she had been sure to tell me. In fact, she had mentioned several times that she didn’t have anybody to date right now — and that she liked older men.

All of a sudden, it was clear to me that she had been begging me to pursue her, but I’d been too clueless to notice.

I have a long history of being clueless with women. I can be oblivious. The weird thing is that I’m super observant with many thing. I’m also super observant in a relationship. But when it’s a matter of a woman expressing interest, I need a billboard with screaming letters saying, “Hey, you idiot! I’m in love with you!”

When I was a freshman in college, I had a political science class with a beautiful sophomore woman who was also a cheerleader. We talked a bit before and after classes during the semester, but I didn’t think anything of it. She was just a good-looking woman being nice to someone out of her league.

When we took our final, she waited outside the door for me to leave. We talked about the test as we walked to the parking lot. I was parked in a remote part of the lot, but she walked with me, so I assumed she was parked over that way, too.

When we finally got to my car, we stood there talking for a minute and then I indicated I needed to leave. She pulled out a notebook and wrote something. She tore out the page out and handed it to me.

“Call me sometime,” she said as I looked at her phone number.

Believe it or not, it took me a long time to realize what that was all about.

Years later — when you would think I would have found a clue along the way — I met a nice single woman who had a young daughter. She gave me her number and we went out. Then on a second date, we were at her house. I spent a long time playing with her little girl — who was about 3 — and we generally had a good time. After the little girl had gone to bed, we ended up talking about what we were looking for in the future. It quickly became clear that we weren’t a good match for the long term, because our basic goals conflicted. I thought that was that.

When we were through chatting — by which time it was pretty late — I made my way to the front door and she stayed close. She kept touching me in little ways — as she had been while we were talking on her couch — but I didn’t think anything of it.

After I stepped out the door, I turned to say a last goodbye. She suddenly embraced me and pulled me close — her face close to mine. I just gave her a friendly hug and then pulled away to leave. It wasn’t until days later that I realized what she had wanted — and how clueless I’d been.

All I was thinking about is that we had decided our goals didn’t match, so she couldn’t possibly have wanted anything else. Right? But eventually I realized why she held onto that hug — and why she looked a miffed or hurt when I pulled away.

I could go on, but you get the idea.

I’ve always had a lot of confidence about most things. I knew I was bright. I knew I was talented. I knew I could do anything I set my mind to. But a woman’s possible romantic interest turned me to jelly. Beautiful women were my kryptonite.

This has led to me not pursuing women who I know how I should have at least pursued — and it’s lead to half-hearted pursuit of someone I wanted.

About 15 years ago, I met a young woman who I was crazy about and wanted to pursue, but she eventually told me our age difference was too much, so I left her alone. Skip forward nearly 10 years. I had noticed that she had been involved with a guy for some time, but then all mention of him disappeared from her Facebook page. I still wanted to pursue her and I wondered if the passing time would make the age difference matter less. I invented some reason to send her a message, but when her reply was nothing buy a polite response with no encouragement, I gave up.

Eventually — after she was married and it was too late — I confessed to her that I had been interested in pursuing her again. It turned out that she hadn’t intended to brush me off. She didn’t even remember having thought the age difference had been too much. She said she wished I had pursued her.

Reviewing my long history of being clueless with women makes me cringe.

I’ve grown and changed a lot over the years. I know myself better. I understand where I came from far better. I’m more mature about understanding what I can accomplish and what things matter to me. For the most part, I’m really happy with how far I’ve come over the years.

But in this one way, I’m still a terrified 16-year-old who’s certain no girl will ever love him, much less want to marry him. If you ever decide you’re interested in me, you’d better tell me in no uncertain terms — because I’m clueless enough to miss what might be obvious to everyone else.