I told this guy who wrote to me that I do not remember ever actually meeting him, even though he says we had a great conversation.

He wrote back. He was relentless, so I asked him to tell me a bit about himself. He wrote, among other things, “I’m the guy you want to date.”

It was such a direct response. And I like direct. Plus, he was going to be in Madison. That never happens.

Two days before the date, I checked him out on Facebook.

Then I wrote him an email. “You are way too young. I can’t go out with you.”

He wrote back, “You should know more than anyone else that online identities are deceiving. And anyway, I’m older than you think.”

That was a good response.

So we agreed to meet at a diner. For coffee. I walk in, and right away I know who he is: The guy with the backpack.

We sit down.

I lean across the table, and in a low voice I ask, “How old are you?”

He says, “I knew you’d ask that.” He says, “Twenty-five.”

I look around to see if people at the diner are staring at us.

He is surprisingly interesting. He’s semi-pro in an odd sport, and he has a business plan to create a quirky application for the iPhone. We talk for an hour.

Outside he says, “I’d like to see you again.”

I think that’s hilarious. I mean, I can’t believe a 25-year-old wants to see me once, let alone again. And I can’t imagine how things will unfold. So I say, “Okay.”

On the next date he knows the chef of the restaurant, so I think he does not totally have to pay for dinner, which is good, because he doesn’t have the kind of job that could pay for this kind of dinner.

We talk about social media. He tells me about conferences he goes to in warm places with hipsters who live and breathe technology. Topics like iPhone applications for crowdsourcing get me excited. I am a sucker for someone who can teach me something.

After dinner he wants to go to a bar. We walk to one he can’t find, and I am freezing and complaining and he slips his arm around my waist.

I think it was warmer with his arm there. Or maybe my body started sweating from the stress of walking through Madison with a twenty-five-year-old.

The bar is loud. I lean over, close to his cheek, and say, “I have to leave now. My ex-husband is with the kids and I told him he could leave at 10:30.”

The twenty-five-year-old looks at me.

I go on. “Maybe we need a plan or something. I mean, I need to either drive you back or drive you to my house.”

He says, “Let’s go to your house.”

In the car I tell him it’s crazy to take him to my house.

I look over at him. He looks back.

“Okay,” I say. “Okay. My house.”

In the car I imagine him at my house, and he will have to take a cab home, and it seems like a pain. And the potential for awkwardness is huge.

At a stop-sign on a dark road, I say, “I’m turning around and taking you back.”

He takes his seatbelt off, leans over and kisses me. It is a very good kiss, slow and soft, and a little bit wet. And it seems very hard to do that when the whole rest of the evening is riding on one kiss. I reward him by heading toward my house.

My Ex is at the house when we walk in. The guys I work with are the same age as the twenty-five-year-old, and they’ve been to my house late at night many times, so my Ex assumes I work with the twenty-five-year-old and he’s chatty.

When the Ex leaves I take the twenty-five-year-old into the kitchen. I tell him, “It’s my son’s half-birthday tomorrow. He needs cupcakes for school. I have one more batch to make.” Then I start dripping gooey batter into superhero foils.

The twenty-five-year-old is patient. And anxious. I sit on the counter and watch him watch the cupcakes, and then when he’s within reach, I scoop him over to me with my legs.

We cannot kiss too much because there’s no extra batter if this batch burns. I am focused on cooking.

Then we go upstairs.

When he pins me against the wall, our age gap dissipates.

Fast-forward: I have seen him again. Though not a lot.

I’ve seen him enough to get flashbacks to when I dated guys a lot farther along in their career than I was. It was exciting. They knew a lot more about sex than I did, but you equalize on that pretty fast. And then, what’s left in the inequality department is career stuff. And I could always figure out how to get stuff from them.

It was exciting to be the young girl who the older guys want to help, and date. At the same time. I was never sure how much I wanted either offering, but I knew that together, they were intoxicating. I want to see what that’s like from the other side.

I am nervous with the twenty-five-year-old because of that. He asked me why I’m not following him on Twitter and I told him I forgot. But I didn’t forget. I read his feed all the time. But I didn’t want to look like a stalker, because so many times in my life, the older guys felt like stalkers to me.

The twenty-five-year-old asks for a lot of advice with work. He is, after all, working in my field. Almost everyone he has needed to get in touch with is someone I’ve had lunch with. I’m also very hesitant to ask friends to help a guy I’m having sex with. In the past, when I have seen executives do this with marketing girls (I have seen this a lot, actually) I have been embarrassed for them.

So I have not helped him that much, honestly. And in bed one morning I say, “How come you haven’t asked me to get you a job?

He says, “The thought’s occurred to me. I figured it would eventually come up.”

I don’t say anything. I don’t want to help him get a job. I want this to not be about all the stuff I could do for him. But all the older men I dated when I was his age were people who helped me with my career; they it did gracefully, and I was so thankful.

I started writing career advice because in my career I found myself constantly in situations that made the old workplace rules seem irrelevant. I realized the workplace had changed, and I wrote advice as I lived through it so the next wave of workers would have a relevant guide.

Today I have an amazing network of men and women who help me guide my career. But periodically I find my career lands me in a spot I have not been before. Right now I feel clumsy. Like the people who write long emails to me, thinking I have not heard their career problem before.

When I started writing career advice, the questions I answered were is job hopping bad? Is being lost bad? Today I find myself wondering: When women get power at work, do they use it like men do?