I have a problem and of course seek your advice. I'm attracted to an older coworker (3 years) who is separated from her husband. We have become great friends, and I would like to intensify our relationship. But I'm not 100 percent sure of her opinion of me. So what is your advice on this possible dating situation? Is it against all common sense for a guy to date a woman older than him? As always, you have great advice, but I hope your advice is what I want to hear.
— Worried about sexual harassment
There are so many things to address here. But I have no problem in finding a place to begin.
Older woman? Three years is not an older woman. It isn't even an age difference. You two were probably born under the same presidential administration, played with the same kind of toys and danced to the same music. You make it sound like you calculate on a computer, and she uses an abacus.
A good friend of mine is engaged to a man who is almost four years younger, and I'm certain that age never came up once. So, first and foremost, get over the age thing. It takes at least 10 years of difference before it can even begin to become an issue.
Second, it is a good thing that you are worried about sexual harassment. I don't think it's going to come down to that, but you definitely should find out if your place of employment has any restrictions on coworkers dating. Many places do not allow it, and for good reason. If the relationship doesn't work out then you two still have to see each other every day and a frosty work environment is an unproductive one that employers may want to avoid.
Do you two have to see each other every day? Even if you were allowed to date, then you must consider the awkwardness if it doesn't work out. There's also the factor of being the main topic around the water cooler among your other coworkers. They will talk about you and your love interest, and that may also interfere with your comfort level.
Here's the most important part. You might curse my name, but eventually you'll realize I'm correct.
You said your woman is separated? Whether it is a legal separation or just an agreement between her and her spouse to take a break for a while, the woman is married. Are you paying attention? She is married. Until the ink is dry on the divorce papers, she is a married woman. Any activity beyond friendship constitutes adultery.
An even sadder fact is that if you are the next person she dates then you are — say it with me — the transition man. Because of the timing, any relationship she has now will be closely linked with the breakup of her marriage. You might be a shoulder to cry on and even get some good loving out of it but, in the end, she will want to extricate herself from anything that happened when her long-term relationship failed. And that means you.
Let me tell you something you already know: Not all great friendships lead to something more. You were worried about the age factor and that turned out to be the only issue here that really isn't an issue. The problem is simple. She's married and you work together. Keep it at a friendship level. A new woman is a lot easier to find than a new job.