I'm 26, she's 46, and we work in the same building but for different businesses. We have casual conversations when passing by and see each other 3-4 days a week. Last year, she invited me out with her and some others from the building to a bar, and we've went out about 4-5 times since then, always having a good time. It seems like she's in a phase of her life where she enjoys going out, having drinks, and keeping things casual, which works for me since I'm focused on my future and not looking for commitments right now. I find her attractive and want to take things to a more physical level.

Despite the age gap, I make sure she knows I find her attractive by complimenting her when she calls herself old or when I notice her efforts like new hairstyles. We even share the same birthday, which I see as a potential connection point. I try to avoid mentioning the age difference and focus on making her feel good about herself. Shes complimented me before as well

There was a moment a few years ago where she offered me some extra condoms she had in her car on a ride home, and I missed what could have been a risqué opportunity. I should've said something like "we should try out some of these condoms and see if they’re working correctly," lol even though it's corny. I always wonder WHAT IF I had said that, where it could've gone. I always think back to that and wonder what could have happened if I had been bolder. It's those little moments where I feel I've missed out the most, not making subtle comments or taking the chance to say something a little suggestive. It kills me thinking about it.

She's also given me rides home and mentioned how close we are, but I haven't mustered the courage to suggest we link up just the two of us.

Lately, I've been overthinking things and talking to her less, feeling nervous about expressing my attraction and not wanting to waste my chances. I'm considering saying something like "if only you were into younger guys" to gauge her reaction, but I'm unsure. Any advice on how to proceed and see if this could actually happen