Navigating Older Women

Since I’m not allowed to post on the off topic forum for some reason, we’ll give this a try. So it’s my first year in the workplace and I’ve had some great experiences thus far. The topic of today is how to navigate older women in the workplace, especially those who are maybe interested in you? Anyway, this is all anecdotal of course, so I’m just here to share my experience. 

My experience:

This one woman that looks like a slightly older version of Megan Fox (late 30’s, maybe 40) got hired on a few months ago in a different department. I didn’t meet her until a couple weeks later whenever I had to drop some documents off at her office. She started with a “thanks sweetie” and of course I said “sure thing” like a casual gentleman. As I was leaving, I thought “hmm she seems nice”. Fast forward a few weeks, she sees me in the hallway. She says my name and I turn around and she places her hand on my shoulder and tells me that she needed something else from me that needed done ASAP (a certain document, get your head out of the gutter). In meetings, she’s always sitting right next to me. Last meeting we were in, she sits right beside me and says “I’ll try not to talk to you” and I was like “ok” and gave her the Patrick Bateman lip smile. I look over and she’s got a ring on her yes I do finger. I’m thinking “she’s just trying to make new friends.” 

Fast forward to the end of summer, I see her walking as I’m running down the street almost by my house. We talked in surprise as neither of us knew we lived on the same street lmao. Next week at work, she’s asks for my number through e-mail so she could send something that she couldn’t through e-mail. She didn’t end up sending me anything so I emailed her the day after to see if she tried sending me anything and she said “nevermind that, we’re good.” A couple of weeks go by and I catch her walking again on the street and she stops me and asks if I could help her move the couch in her house this week. I said “sure, no problem” and asked one of my friends to see if he could help me an evening he was free as I didn’t want her to do any of that kind of work. Whenever I went home to change after work the day we went, I thought “doesn’t she have a husband or someone to help her?” Anyway, I’m in the house doing some scenic investigation as I’m making my way through the house with her and my friend, looking for photos of her supposed husband in my mind. Saw nothing, just photos of her, her son, friends, and other immediate family members I guessed. My friend and I get everything that she wanted moved in a decent amount of time. Afterwards, she made us dinner and we all ate the table, including her 12 year old son. Once we’re done and talked for a bit, we leave and my friend says “who is that?” I said it’s just a coworker. He was like “damn, is she single?” I told him I honestly don’t know lol. A couple of weeks go by and I receive a phone call. It’s a nice Thursday evening after coming home from work and putting the dishes away, I look at my phone and didn’t recognize the number so I ignored it. They called again so I answered and it ended up being her talking to me in a hurried voice, apologetically asking me to watch her son while she had things to get done, of which I didn’t ask what it was but I replied with a “yeah I can do that no prob.” I was comfortable with him coming over to my place as I already somewhat knew him and lived alone. We ended up having a great time actually. From playing GTA 5 to skateboarding out in front of the house, we had a blast. It made me think of all the cool things I wanted to do at that age as I have a strict mom. Fast forward a couple days, she wants to go out and get a couple drinks since her son wasn’t going to be with her for the weekend. At this point, I didn’t know if I was turning into her male best friend or something else. We go out for not even an hour and she’s already ready to go home and wanted me to come back and kick it at her place. So I proceed with her plans and now I’m in her bed watching wedding crashers, since it was or still is on Netflix. I’m thinking “oh my god, what am I doing lmao!” I wasn’t even planning on any of this happening and you can already guess what happened. I haven’t got laid since I was 19 because I wanted to go through my 20’s not doing any of that just so I can have peace in mind when I’m in my 30’s or older if shit goes bad I can at least say “well I didn’t waste my 20’s talking to women”, now look at me. I’m trying to refrain from all that since I want to go to b school and do IB. Anyway, I’ve been staying with her every other weekend have been doing errands with her and her son. The last time we hung out, she asked if I was going to spend thanksgiving with her? I told her I’ll let you know, I have a few families to attend to. Not sure what to do, she’s really cool and so is her son. I don’t want to be going to his mandatory chorus concert and seeing my teachers from 10 years ago questioning why I’m there. What would you do from here on out? Trying to navigate this thing strategically as I have some goals I want to achieve in my life. Also, how am I going to handle this at work? We hardly see each other so that’s a plus.