replied 7 years ago.
Hi again, Matt, and thanks for your reply with additional and helpful information about your situation.
I understand why you feel it's risky to ask these ladies out, not knowing if they are single, involved in a relationship, etc., so the first thing you need to do is chat them up, be friendly, and casually ask questions within your chatting to find out what their 'situation' is. For example, to the bar lady (now, I'm not sure if you mean the lady who works behind the bar, or a lady you meet at a bar), ask, does your husband mind when you come here alone? OR, if she's the lady who works behind the bar, ask: 'Does your husband mind when you come home late?' you know, because the bar is open late. If she says 'I'm not married' or 'I don't have a husband', then follow with, you're so attractive, are you seeing anybody; do you have a boyfriend? Then, take it from there, depending on her answer. If she says she's dating but doesn't have a boyfriend, ask if she'd like to meet you for coffee sometime because you'd like to get to know her better, and ask for her phone number.
You don't have to ask her out immediately. You can talk to her a few times, get to know about things she likes to do, like going to movies, bowling, ice skating, museums, etc. Also, ask about her work. You can share your interests, too. Each time you're there, get to know more about her until you feel confident enough to ask for her number, then call her and get together very casually, at first. Coffee/lunch, is great for a first meeting.
With the checkout person, the same idea applies, be friendly, smile, say she looks nice today, she has beautiful eyes, hair, etc., on different visits, until you feel you can ask for her phone number. You can even say, 'If you're not attached, I'd love to take you out sometime'; if she says, no, I'm sorry, I'm married, or I'm seeing someone, then you'll know her situation.
What's most important is that you have to gain some confidence in yourself, first, and then you'll feel confident in asking them out. Ask yourself: what's the worst thing that can happen? She'll say no. No biggie, you'll move on to someone else you find attractive. If you're shy, practice in front of the mirror, how you will look/dress, what you will say, until it feels very natural to you. And a smile goes a long way! Always smile, be pleasant, give a compliment, but be sincere, and if a lady is single, she'll be happy to accept your invitation to coffee, etc.
I wish you much good luck and please let me know your thoughts and if you would like to discuss this further.