I have an odd dilemma-asking out a co-worker

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I am thinking of asking out someone I work with. Now, I don't have much of a physical attraction to her but I do enjoy her company. I even know what I would do for the date. The problem is that we have worked together for five years and so if it goes wrong it would be difficult to deal with as it is unlikely either of us is going anywhere soon. I don't take rejection well either and so if that happens it will put me in a depressed state for the next 6 months or so. We are also 13 years apart in age (she is younger than me), so that may be a deal breaker too. I don't know what to do since I hate being alone and she is a person I care about, I just don't know if it's enough to attempt this. I am over analyzing it a bit too as I am trying to figure out what you do on a date, where to go, what to say, what the proper protocols are, etc. It probably doesn't help that I haven't been on a date in about ten years.

If you cant handle rejection, you'll be in an awkward position if she does say no. Personally I don't recommend dating coworkers anyways. Even if the relationship succeeds, that can have a negative impact on the work environment. And should the relationship dissolve, that can create even greater problems. I work in a place with a lot of people and I've seen countless relationships form, fall apart, and next thing you know someone is quitting because they can't stand to be around that person anymore.

If you like your job, and would not want to end up looking for work elsewhere, I'd say enjoy them as you do, and don't rock the boat. Keep your job, and find someone on the outside.

The workplace is a very common place for relationships to start. There are a lot of happily married couples at my company.

I can't give you any dating advice because like you I haven't been in a date in over 10 years. However, one thing I wonder about is that you say you aren't physically attracted to your co-worker. Maybe physical intimacy isn't very important to you, but the way you describe your co-worker, she sounds more like a friend than a romantic interest.

Why do you want to date someone you're not attracted to?

Consider the impact to your job if you start dating. Some companies have policies affecting this and some are hostile to it.

I had problems from asking out women I've worked with. Being around them was difficult after till they quit; I'm sure they didn't quit because of me but I was glad when they did. I'm not saying not to ask her out thou. I've seen other relationships start at work that seemed fine in the workplace; be careful & think about things a bit. It seems like you & her might have a good work friendship so perhaps you can progress it to more; you could start by inviting her to do something with you after work for example.

Dating in the work place is always a real gamble. I've always been against it because I certainly wouldn't want to have to see my ex-girlfriend everyday and I certainly wouldn't want my work life and personal life to become one. It would be very distracting and make my job much more stressful. I think the only time dating at work is okay is if neither of you have a particularly good job that you value. If you're both working at a temporary low paying service industry job, then it's much easier to bail out of those jobs if things turn disastrous. But if your are talking about a job where it pays well and is your career, don't do it. With how bad the economy is, that's too big of a gamble. We can no longer find another job right away with a drop of a hat.

The thing is, I have always liked her as a person which to me is more important than the physical. Plus, my physical attraction standards are ridiculously high. As for the type of job, yes it is service industry. She makes minimum wage, but I make tips and do VERY well at it. I probably average $12-20 an hour (depending on the time of year), a good pay rate where I live. What I am thinking I might do is just see if she wants to spend a day together. As I make 2-3x as much as she does, I have no problem paying as it will be no great strain to do so. Then again, maybe not. It is an odd situation, one that is made much more difficult by my own lack of experience and social opportunities. It's also odd to meet someone in my business who is not into drugs, heavy drinking or smoking cigarettes, so she ticks those boxes. I just question what standards are realistic to expect at my age, given the limited number of people I could possibly choose from. I am not really interested in women my own age because I find their maturity and life experience intimidating. The one deal breaker though is that she does not share my faith, something I consider critical. Everything else I could deal with.

Sorry for the meandering rant, but I really have no clue what to do at this point in my life.