Sanctifiable,
I’m a regular visitor to
Catholic.com but I just now became a registered user so I could give you a response and some practical advice for your situation. The women here will agree with what I’m about to say.
First, be confident in who you are. If she is turned off because you’re “too religious”, then she’s not what you need (or what you should want). Period. You mentioned she’s a single mom, so your faith ought to be a plus for you since the well-being of her child should be one of her top priorities, especially in regards to teaching her child morals.
Second, DO NOT let her looks or beauty be a controlling factor in how you act or be your primary interest. Looks are nice, but not everything, that’s for sure. Read the story of Samson and Delilah in the Old Testament.
Third, as is often the case and a general rule, when a woman has made clear through a number of hints that she is interested in a man, that man has a limited window of opportunity to make a move. If the man doesn’t make his move, that window of opportunity may be shut forever. Some men think that the woman will always remain interested, and these men will sometimes date other women and think they can come back to the first woman and exercise their “option” only to find out she moved on a year ago. I’ve seen it happen time and again. Respect her and don’t leave her hanging. A woman may always remain nice and polite, but she still could have moved on. But, there are always exceptions. The last thing you want is to do is ruin an opportunity because you failed to act.
The best thing is to ask her out sooner rather than later. When you do ask her out, it doesn’t have to be anything big, even a trip to Starbucks is nice and cheap. If the initial one-on-one thing is a bit much for you, then ask her to accompany you for a social evening with some of your friends.
Since she knows you and you talk with her at work (even though it’s only work-related), she probably has a general sense of your personality, so I wouldn’t advise trying to change anything dramatically (she’ll notice).
For me, I can always do the dinner or Starbucks thing. As for another activity, I love to go watch live music. I also love to shoot firearms, and a trip to the gun range to target shoot is not expensive. Some women are afraid of guns if they’ve never shot them, but once they are shown how they operate, that fear goes away and they really enjoy it. It’s like throwing darts with a dose of gun powder. You would be surprised how many women have licenses to carry handguns.
But whenever you do ask her, don’t be concerned whether your voice is in the key of A or B or other such nonsense. Confidence always counteracts an appearance of desperateness or the impression you’ve already decided you want to get serious before the first date. A desperate-like impression isn’t helpful and is a turn off for a lot of women. But she’ll get the message pretty quick that you’re interested when you ask. Women are very good at reading men’s emotions and personal attitudes. I would bet she already knows.
If she declines, tell her you just had to know because you had an interest, but now you can move on. She’ll respect that. If she is a mature adult there should be no problem at work.
Lastly, think from a theory of abundance. Communicate to her the unspoken message that you know there are a lot of fish in the sea, and you’re not putting all of your eggs in one basket, but this is where you are right here and now, and that she is the one who has the opportunity to be a part of your amazing life.
And, keep in mind your conversations have only been work related. Beyond that you don’t know too much about her (from what I’ve gathered). NEVER try to create an image in your mind of her that isn’t there or real. You’ll find all that out as you get to know her, which is the point of the initial “get togethers”. It should not be as much about you trying to figure out whether she’s into you, but you need to find out more about her, too.
Remember, it is your confidence in who you are that takes care of most of these things I mentioned.
Good luck.