Tread Carefully

By Nick Campbell:

I’m currently 6 months pregnant and no longer with the child’s father. We broke up before I knew I was pregnant. Its a guy at work I have a serious crush on. I’m 28 and he’s in his late 40s. I took a look at his hands and noticed that he wasn’t wearing a wedding ring so I’m assuming he’s not married. I decided to take a risk and hit him up on a business networking site. So far he is responding and we are have light conversation. I ask him personal questions without being too much or coming off as inappropriate.

I’m very shy and cautious simply because he is the boss of my boss and we work together from time to time but not so much where if we started to date it would be obvious to others. I asked my closest friends at work what I should do. Should I ask him to lunch or straight up ask him if he’s married just to be sure? I don’t want to continue to beat around the bush with emailing him back and forth. The guy I’m interested in seems like a very honest person and straight forward guy. He jokes around much like the rest of us in our department but is about his business when need be.

My co-workers advised me to leave it alone simply because I’m pregnant while others advise me to “just be careful”. I have no problems putting myself out there when it comes to dating but I have never approached a co-worker before; especially someone I sort of work under. I don’t even know that he’s knows I’m interested. I think he assumes that I’m just being nice.

How do I let him know I’m interested? Do I just ask him out? I’m not even sure it’s the right time since I’m pregnant. People tend to not want to talk to anyone who is pregnant. I’m more interested in getting to know him but don’t want to push too hard in making him respond by asking a whole bunch of questions.

What do you think I should do??


Nic’s thoughts:

Congrats on your pregnancy!  Well, you’re walking a tight rope indeed. Being pregnant and actively dating can be a challenge. Some men will be ok with it, some won’t. It depends on what they want. If it’s sex they want, they will be all over it. If they wan’t more, it might be an issue. I say that because you’re obviously interested in this man, and being pregnant will change the dynamic. As long as you can deal with that you can toe the line just fine. You’re in a tricky situation because you’re faced with a double edged sword here. First off you’re not supposed to shit where you eat. This is your bosses boss were talking about. Which brings us to the other edge of the sword. If he is in fact interested he’s going to be put in a compromising position. No matter how interested he is, this man will oblige by the same rule I mentioned earlier. Most people in those high management positions seldom risk their careers over a workplace relationship. If the situation ends up working out in your favor, it’s going to be all or nothing. Be very careful if the situation starts to muddle in the middle. That’s where you’ll find trouble.

So if you decide to pursue it, how can you express yourself and maintain your professionalism? Well, business lunches are a nice setting for it. You should be at your best when it comes to etiquette. But most importantly look for the cues, because a man will show his interest. That’s if he’s interested! But if you’re on the fence about it and can’t put your finger on it to gauge his interest, then simply ask if he’s married. Men know that question only comes up in two situations: When a woman is trying to sell us something, or if she’s interested. He’ll know the deal, and at that point he’ll either give you the green, yellow, or red light. He’ll give you the hint you’ll need and he’ll take it from there. But I’ll add to the chorus on this one. Be very careful…

Best of luck!


About Nick Campbell

Nick Campbell has written 163 post in this blog.

A modern day gentleman who loves to explore all aspects of relationships and discuss problems this new generation faces in love. Born and raised in the Bay Area, well traveled and cultured. Single Dad, tech connoisseur and news junkie. Drop a line if there is something you'd like discussed!

  • While “parents need love too”, I don’t think dating should be a concern and you’re having a baby in 3 months. The demands the new baby will put on you is going to affect your dating life. Wait until you get settled into a routine with the new baby before you try to add dating to the mix.