I don’t want to be creepy

We will chat today at 1. You'll get a letter tomorrow and updates on Friday.

I like it when this letter writer says "Facebookians." Sounds like a secret society -- the Order of the Facebookians.

Hi Meredith,

I'm in my late 40s and my wife passed away about seven years ago, leaving me with two young daughters. It's been a process, but through a lot of effort and (preemptive) counseling, I think all of us are fairly stable. Basically I don't take any day for granted, and through telework and judicious vacation leave I'm there for my kids as much as possible.

I haven't pursued anything romantically in this time. I'm just trying to get a handle on single parenting while honoring my wife's legacy. While I think I'm more ready now, I'm concerned that my romantic instincts are way off.

I bring this up because I think my daughter's teacher from last year, "Cindy", has said some odd things. Cindy's about 28, and very lively and energetic. This is someone who isn't lacking for people to "friend" her, as the Facebookians would say.

I volunteered last year in my daughter's class. Cindy said at the end that she'd love for me to come in again for her kids this year, which was just polite talk. But I saw her again at a function, and she reiterated that and suggested we meet for coffee to lay out a plan. Later in the evening we were talking with a group of people, and she seemed eager to note how she would love to see an art exhibit I said I might try to see at my lunchtime. It just seemed like there might be something there.
Thing is, I find myself starting to think about Cindy. I can't believe she'd be interested in me given the complications in my life and the options she must have. I just don't have the flexibility to court her as you normally would expect, as that takes time from my kids. So, what do I do? Is this just a fantasy I have, one that's normal for a widower getting ready to move on? Or might there be something there? I just don't want to come off as some sort of creep, so my inclination is to put this out of my mind. Thank you for any thoughts you have.

– Wondering, New Jersey

You won't seem like a creep if you're honest, W.

Just put it all out there. "Cindy, I'd love to hang out with you -- but is that OK? Would it be a date? Should we be friends? I'm new to this and it has been years since I lost my wife. I'm worried about saying the wrong thing and making you uncomfortable."

If Cindy is interested, she'll let you know. And if she's only interested as a friend, she'll tell you that, too. She's warm. She's not shy with you. She wants to know you better. She's going to help you through this awkward conversation.

At the very least, she'll be good practice. Don't put her out of your mind. Don't shy away from her because dating is scary. You're a human, not just a dad. And this is exciting, right?

It's almost never wrong to tell someone that you have no idea what you're doing, as long as you're being sincere.

Readers? Is Cindy the real deal? Does it matter? What should he say to her? Words of encouragement from the Order of the Facebookians? Discuss.

– Meredith