Falling for my married boss

Two things:
1. Boston University is hosting a very fun panel on Tuesday night about love, Love Letters, and college relationships. It is open to all college students -- not just BU folks -- so if you're matriculated anywhere, please forget all Beanpot rivalries and attend.
2. I'll be teaching kids how to write advice next Friday as part of a February break program at 826 Boston. I want kids to be answering real letters, so if you have a problem that you want the 12-and-up crowd to answer, please help by emailing me your dilemma to meregoldstein at gmail dot com with "826" in the subject line. This will be a very fun activity for these kids, and I'll post some of their advice. Keep the subject matter family friendly, please. Make them think. And if you have a Boston kid who's going to be bored next week, feel free to sign them up.

Hi Meredith,

I'm in my mid-20s and for the past eight months have been working for a small business in the industry I want to specialize in. My boss is about 20-ish years older than me and established enough that his name is worth dropping in some circles. I'm a friendly person (or so I like to think), and he is always cheerful and open. We have a very easy working relationship that has extended to a mentorship. Although there is a big age difference, we have many similarities -- our backgrounds, ambitions, sense of humor, family loyalty, etc. Over the past several months I have come to regard him not just as my employer and mentor, but as a good friend.

In the last few weeks, however, it has become increasingly clear that my boss is interested in taking our relationship to the next level. He is charming by nature, and flirts with practically everyone he meets, so I was caught off guard when he became more flirty than usual one night after work. Up until that moment, I had never even considered him in a romantic light, partly because he is my employer, and mostly because he is married and has a young child.

At first I thought he was just lonely and in need of company (he has to stay in the city alone a lot) and I just happened to be nearby. However, he's made it clear that his interest in me is not purely sexual. I haven't felt harassed by his attention (I've done the corporate harassment training and know what is inappropriate). It honestly feels like he is pursuing me as if he were single and wants to date me properly.

My first reaction was knee-jerk -- to get away as soon as I possibly could. Regardless of how this all plays out, I have a lot to lose. The industry we work in and his reputation in it are such that he could damage my career prospects, not just by firing me, but also by blacklisting me in academic and internship placements. Obviously, I'm not the first girl to find herself in this situation, and it seems like the standard is that the junior people are the ones who have to quietly disappear. Of course, his family is also on the line, but I do wonder if this is even an issue for him, given how blatant he's been thus far. He often mentions his child, although rarely talks about his wife.

What makes it hard to go against my first reaction is that I'm finding it terribly hard to think badly of him (here's the part where I feel like a horrible person). I've considered him a close friend for a while now, and I'm certain that he feels the same. We've shared both professional and private worries, and I have always felt at ease with him. We have a natural, comfortable dynamic to the point that other people we've worked with have said that they've never seen two people more well-matched. Apart from his current circumstances, he is someone with whom I can easily see myself becoming seriously involved. He has told me that he is happily married, but is confused about where I belong in his life.

All this being said, I like to think I am a good person with a healthy set of morals. I have been cheated on before, and I don't think I could ever be responsible for making another woman feel that way, especially when there is a child involved. I've turned to friends for advice, many of whom have not been supportive. I've been called and accused of lots of unpleasant things, which has been upsetting to say the least. My guilt at what he is proposing does not change my feelings for him -- it's just added to the jumble of emotions inside my head. I could really use some constructive advice on how to move forward. Thanks in advance to you and the readers.

– Possibly the other woman, NY

I'm so glad that you emailed us now, PTOW. So many letter writers check in after they've become the other woman. I always wish I could throw them in a Love Letters time machine and give them pre-affair advice.

But you're catching yourself and asking big questions at just the right time. You know that a great professional friendship has evolved into a romantic relationship. You know that you like that relationship -- but that it's very wrong. I understand that you're charmed by this guy and that you're similar in some ways, but ... you're actually very different. Like opposites.

1. He's married and you're not.

2. He has a kid and you don't.

3. He's a pro in his career and you're just starting out.

4. He's 20 years older than you.

He did you a big favor by telling you that he's happily married. Now you can say to him, "I think it's wonderful that you're in a good marriage and I have no plans to spoil that. Let's focus on professional respect. Let's be responsible, trustworthy, professional adults." Set boundaries and respect them. No hanging out outside of work. No date behavior.

You emailed us now because you know what's right. Frankly, even if he wasn't married, I'd tell you to stay away. Mentors and bosses aren't supposed to be boyfriends. And you don't want to be with a guy who "flirts with practically everyone he meets." Ask those smart friends of yours to help you look for better dating options. Keep yourself busy after work. Read that list of differences over and over and over.

Readers? How can she stop this relationship from progressing? Is this a sexual harassment issue without her knowing it? What is happening here and how should she proceed? Should she report this to anyone? Discuss.

– Meredith