Hello Community, I'd like to ask for people's advice on how to approach getting out there and trying to meet more people in person through connections I know, such as friend and co-workers etc..

A Little backstory first if I may:

I've worked for a cleaning company for about 5-6 years now and have worked with the same folks for a long while and I really like the crew I've worked with, they're really good people and we all get along great minus one co-worker nobody likes haha so, the shop fell on hard times during the pandemic, as most places did during that time.. I basically had to look for work elsewhere and I ended up working the electrical trade for a while and around that same time their was a change of hands between the new and previous owners of the business.

The original owners came back and had a dispute with the old ones blah blah and so our new boss ended up being a woman around my age (maybe you can see where I am going with this lol) And she's very attractive and super nice and a very friendly person, I first met her at a Christmas get together the company was having, to bring everyone together and be festive and enjoy the holidays..

I'm not very outgoing or very social and struggle with social anxiety, but I knew attending would be good for me and in the end I am glad I did..

So, I put on something nice and drove to the Christmas party, put on my happy face and did my best to be appear confident and social. I got there kind of early and there wasn't many people there yet, so I decided to go around the room and introduce myself to a few people and then I noticed our new boss standing next to some older lady, who I later discovered was her mother (I am slow to pick these things up). And the funniest thing happened as I went up to introduce myself, she turned to look at me adn her face turned bright red and she started stuttering and couldn't form her sentences properly! I thought it was the cutest thing and reminded me of like a high-school crush or something, I cherished that moment to this day and I was so surprised to have had that affect on her, apparently she'd found me attractive, so that was very flattering..

Fast forward to post pandemic a few months back in April 2022, I was gone for a good year or so from the company and left to do my own thing as a Handyman, among other things. I got a call from my former boss, the one I met at the Christmas get together, I will call her Janice for now on to protect her identity. She asks if I could come back to help out while a coworker was out of town on vacation, she's also told me in the past that I was free to come and go as I'd like and there was always a place for me with the company.

So I agreed to come back and help out and that brings me to today, doing both my side business and working for my former company again, and as I sat down with a long time coworker of mine, I had a revelation, as we got on the topic of our boss Janice, I began getting a flood of nostalgia and memories of all the interactions I'd had with her over the years, the talks we've had, the comments made, specific words and phrases that I still remember to this day,the Christmas get together etc.. and I saw an opportunity, I asked myself; why am I doing all this stupid online dating? when I have amazing opportunities sitting right there in front of me? It's foolishness..

I told myself, just look at your brother.. he met a nice girl from his work, why can't you?.. I see all these missed opportunities I've had over the years with friends who brought with them really nice, attractive girls to all the parties we've had and I never once bothered to approach out of fear. Not even making the attempt, is far worse than failing in my book. So as part of my vow to get out and be more social and not be such a shut in, I decided to brave the winds and ask Janice if she'd like to do something outside of work together..

So, this leads to my question: how should I approach this? I have her contact saved in my phone.. should I message her, call her? or meet her in person the next time I see her at the office? secondly, what should I say? how should I Segway or steer the conversation towards asking her out to lunch or for a coffee?

And if she decides not to do that, there are plenty of other attractive girls at the shop, maybe I can approach them? or even network with other people I know?

In fact, when they asked me come back and help out again, they sat me down with a really nice girl that was their new sales rep.. and I was honestly going to ask if she'd like to get together sometime outside of work, I really liked her and she has this aura about here that made me feel comfortable, she was so friendly, and nice, social and outgoing and very attractive. I later discovered she was already with someone and had a 7 year old. But I learned that around certain personality types, I can get comfortable and be myself with them,I just need to meet the right people.

So please let me know your thoughts/opinions and advice on where I should go from here, it'd be greatly appreciated and thank you for reading!