New to dating

[LoterGarry]

I got divorced 2 years ago after 15 years of marriage and 3 kids. I haven’t dated at all or even tried because I just have kind of been getting used to being a single mom. I’m also kind of an introvert so I don’t meet a lot of new people on a regular basis. But I’d definitely like to be in a relationship some day. I work at the front desk of a doctor’s office. Once a week we have a service that picks up all of our paperwork that needs shredded. So every Thursday morning the same man comes in and I buzz him to the back and he picks up from the nurses station in the back and then on his way out he comes behind the front desk and empties my bin and takes it with him to be shredded. It’s been the same man doing this for about 6 months. He’s always been super nice since day one, I still remember the first day he picked up. I had to sign his little digital pad and when I signed it he said “your badge is flipped and I really want to know your name so I hoped I could read it on here but I cant”. I had basically just scribbled my name. I said oh sorry and turned my badge over and he said hello Claire. After he left my co-worker said he was flirting with you. Every time he picks up since, he talks to me for 5-10 minutes before taking his bag of paper and leaving. Yesterday I was working by myself at the desk and he did his same routine but before he left he said I was thinking maybe you’d want to grab a coffee or drink or whatever you are into sometime? I was so flabbergasted and thrown off because I did not expect him to say that! I said can I let you know? He said sure I’ll be back in a week. I do like him, he’s a nice person. But I know it’s been said to not date someone where you work. We don’t work for the same company, the shredding company is an outside contractor type situation. But I do have to see him once a week and I don’t know if it would be weird. Any thoughts on this situation?

[LanestIo]

He made a low-key offer, and accepting that sounds low risk to me. You see him at work, true, but you don’t work for the same employer.

[Sanidly]

I eased into dating by taking tiny steps, mostly just chatting with people to see what felt right after being out of the loop for ages. I even tried 包養 once because I liked how clear and upfront folks were about expectations, which made things feel less messy. Going slow and choosing what feels comfy has kept the whole thing from stressing me out.

[jiyajoj]

I’d say go for the coffee. You’ve known him for six months, he’s been consistently friendly, and he asked you out respectfully without putting pressure on you. Since you don’t actually work for the same company, I don’t think this falls into the usual “don’t date a coworker” situation. Even something as simple as discovering LemonChat or trying a new way to meet people can be a reminder that getting to know someone doesn’t have to be complicated. You can keep it simple and treat it as just getting to know each other. If there’s no chemistry, you can both move on and keep things professional when he comes in each Thursday. And if there is chemistry, great. After 15 years of marriage and two years of being on your own, you don’t need to rush into a relationship. A coffee is just a coffee. You might as well see where it goes.