I’m the Boss. Is it Ok to Date My Subordinate?

 Dear Leather and Lace:  I’m 44 years old and a Senior Vice President at a family-run company. I’m really dedicated to my job and put in many long hours, but I’m also single and still looking for “Mr. Right.” A few months ago the company hired a new Junior Manager. Robert is a charming and intelligent 32-year old (who is also single). He doesn’t work directly for me, but I am the boss of the department. Robert’s cubicle is right outside my office. I never intended to get involved with someone at work, but Robert and I just seem to “click” the minute we met. We both work late, and often find ourselves closing up the office together. Despite our obvious age difference, we seem to have a lot in common. First we there was some harmless flirting which led to some long, personal conversations before we went our separate ways, alone. But last night, Robert took things a step further and asked me out on a real date! I had an appointment so I turned him down with that excuse, but ever since then I’ve been thinking about how it would be if I went out with him. I know that some people say offices romances are too risky, but what if Robert is “the one” and I miss my chance to connect with him? Is it realistic or even fair for me to encourage this type of relationship? What do you think?  

Signed, Laura,  Looking For Love

Lace’s Take on This:  If you’re spending a lot of late nights at the office, you’re supposed to be working,  not socializing. However, it’s easy to understand how people who are literally thrown together night after lonely night, without much opportunity for a social life, might make a love connection at the office.

There is a lot of disagreement about whether dating co-workers or worse, a boss, is acceptable, but plenty of people hook up at work. Bill and Melinda Gates did, and she dated the boss! If there truly is a connection, and you both know it and acknowledge it, it’s something to consider.

But also, you also need to consider if you really have something in common other than you work late together and make nice companions. There is, after all, a fairly significant difference in both your age and your work status. If you met Robert outside of your job, would you really be attracted to him enough to date him? Do you think he would be that interested in you?  Could his main interest in you be that he sees you as a fast track to a promotion?

Surely you realize that if you date someone at work, the risks and penalties can be a lot more than just wounded pride, losing a good friend,  or suffering a broken heart. Under some office policies you can actually be fired for dating a co-worker. Before you make any move toward Robert be sure as “Leather suggests,” make sure you know your company’s fraternization policy. An intended relationship with any co-worker, but especially a younger one, could be considered inappropriate and make the rest of your staff, very uncomfortable. It could also be considered sexual harassment.

Even the most discreet of office romances is bound to become public knowledge soon enough. Can you handle being the prime topic of office gossip? Relationships are fraught with tension but it’s even harder when you are the prime target of wagging tongues and public scrutiny. Even though you aren’t Robert’s immediate supervisor, you may be accused of favoritism by other employees. Robert may be accused of sleeping his way to the top, even if that’s not his true intention. Both of you will need to develop a thick skin to withstand the criticism that might occur. Ask yourself: “Can I really handle having my relationship in the office spotlight every day? How would I feel if I knew someone else in my department was openly dating a subordinate?”

There are also some practical matters. Would being near Robert all day and night be just a bit too close for comfort? How will you manage it if the relationship doesn’t work out and you still have to face each other every single day? Another issue is your work status vs. Robert’s. He is just starting to work his way up the ladder, and you’re already there. Eventually, Robert may have to move out to move up, or even relocate. If you two were still a couple, would you support him both emotionally and perhaps, financially?If there is a big difference in your salaries, could that cause problems? How will you handle socializing with his friends who will be much younger and possibly also even your junior staff? Would that be awkward for him? for you? for them? Would your friends accept Robert as a social equal?

No one would raise an eyebrow if Robert were older and you were younger. And many women are now choosing younger men for mates because they offer something special. If you do go forward and date Robert, you’ll have to work out your issues, as any other couple would. You might also consider that in today’s economy, no job is a sure thing. Either one or both of you might lose or leave your current jobs, be asked to accept an assignment in another city, or decide to get more training and switch careers — and age has little or nothing to do with this.

Beauty is in the eye of the beholder. If Robert genuinely loves you there is no reason to think that he will find you less attractive as both of you continue to age. At this point, I’d guess that part of your allure is that you are more experienced and interesting than his contemporaries. Just be sure that you both know your “must-haves” and “non-negotiables and that you both have the qualities the other is seeking. Intrinsic qualities don’t change with age. Just take the time to find out if the overall substance of your personalities, values, goals, perspectives, and interests are similar enough to stay the course when the going gets rough. If your company doesn’t forbid dating a co-worker, if you feel you can date Robert and not sabotage your career, if you decide that Robert is really “the one” for you despite the obvious issues, and you are genuinely interested and willing to accept the risk, just say “YES!

Leather’s Take on This:  Love is too precious to waste, to find someone who you can be passionate about and who can be passionate about you is the goal to which we all aspire. We spend so much of our life at work,  to eliminate all who work there is like asking us to run an obstacle course with one hand tied behind our back.

The downside here is that it is really uncomfortable to be in an office with someone you have broken up with. The challenge is to make sure you are good enough friends that even if the romance ends you can still talk and interact with each other without rancor. To avoid this, both parties must be mature enough to understand that such rancor is built from unrealistic, disappointed expectations —  you are blaming the other person for something you should not have expected from them.

One of the most important issues here is children, do you want them, does he want them? I am being serious, as if you want them you have to start now. If he wants them and you don’t, you will find it even more difficult to find another life companion 8 years down the road when he regrets not having children.

These days all companies have policies about co-workers dating, and thankfully for you they cannot say no. You work for a family-owned company, so  you are in a bit better situation as public company HR rules do not apply. Get a copy of the employee handbook and read what it says about relationships between co-workers. Most public companies require you to declare the relationship and sign a “hold harmless” agreement with the company (meaning they can not be sued if the relationship blows up). They will also supply each of you with the name, address and phone number of their outside human resources lawyers and any complaints about treatment after the “affair” breaks up are reported to them. As a Senior Vice President if this is not setup at your company then you need to make it happen. Under all circumstances, as a manager, you must inform Human Resources as close to the first “romantic” date as possible. If there is no overt or implied sexuality on the date, that is it is a “friend” date you can let it slide for a bit, but he MUST pay for some portion of the bill (has to appear “Dutch” with the proviso you probably make more than him) and it can not be a strictly romantic restaurant (there is a lot of latitude, there but err on conservative side).

My advice is you need to get to know him a bit better and be sure of his intentions and desires for the future before you take this to ANY kind of physical (including kissing or touching) or implied sexual (through “stimulating” talk) level. Casual after-work dinners since you both “worked late” are fine. If you were not workaholics,  lunch or coffee would be fine. You may not yet see him on the weekends unless you both legitimately go into work first. Just explain to him that you would like to get to know him as a friend before you take it further than that. This puts the dynamics of the relationship in your hands. You must explicitly restart the romantic relationship either through asking him if he is comfortable showing up at Human Resources and making a declaration, or after one of your “friendly dinners” say that if he wishes it, you would be willing to enter into a “romantic” relationship with him. Then,  when you both roll into work, go to Human Resources and fill out the paperwork.

 Lace’s Comments on Leather’s Answer:  Leather is outlining a reasonable plan of action, but how many men in Robert’s position will feel comfortable waltzing into HR with you to make a declaration of a relationship, especially if the relationship is still being formed?  And I honestly think telling a man that you want to be his “friend” will send him the message that this is all you want. If you want to pursue this, you’ll have to handle the initial steps very carefully.  It’s not just what you say, but also how you say it, that counts. That being said, without risk there’s no gain. After a few friendly dinners you need to figure out if you’re work friends, or something more.”