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Should I lean into dating older women? (25M currently dating 41F)


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I'm a 25-year-old guy dealing with some pretty messy relationship stuff right now. A couple years ago, a bad breakup nearly wiped me out financially, and it took me a while to feel ready to start dating again. When I finally did, I ditched all the dating apps and most of my social media - kept Instagram but that's it - and decided I'd rather meet people face to face instead. For context I met my ex who cheated on me with an ex business partner and left with 30,000 dollars they took from the business account.

Since making that change, I've gotten involved in some new groups of people, surfing, painting, cooking class and I keep hitting it off with women who are older than me. A bunch of them have actually asked me out, which is how I ended up with Emily, who's 41. We met when I was just chatting with her at a farmers market while hanging out with some friends and trying some food. 

Things have been going really well between us - we go on regular dates, we're intimate both physically and emotionally, and we talk on the phone pretty much every night until one of us falls asleep. But my mom and my two older sisters won't stop giving me grief about it, especially my mom who's dying for grandkids. Little does she know I'm planning to get a vasectomy pretty soon, plus my sisters are old enough to meet someone and have kids in the future. They're just not into the idea of a serious relationship right now.

My female friends (god bless them) tried hooking me up with people they knew closer to my age - friends, cousins, - but those dates never went anywhere. I'd always end up hearing stuff like "You seem awesome but I really wish you were taller", or my personal favorite "I believe someone like you is meant for me later in life", which left a sour taste in my mouth. They even tried helping me tune my Bumble profile before I deleted it, to no avail.

Enter going out with older women. The tone completely changed to "you're so cute and interesting" and "I feel like I've known you my whole life" and sometimes flat out kissing me on the spot in front of people. Now that I'm going out with Emily, some of my friends make these comments about how she wouldn't really blend in with our crowd if they ever met her. And also sometimes saying I should return to dating apps, which vehemently refuse to do.

But here's the thing - every time I meet someone in person, it always ends up being an older woman, with younger women almost never being interested in me. At this point, I'm thinking maybe I should just roll with it. On top of all that, Emily's been talking about how she could see us getting serious, and I'm definitely not opposed to the idea.

So I guess what I'm wondering is - should I just embrace this whole dating older women thing since that's where I get the most success now? And how do I deal with everyone else's opinions? Do I just ignore it all, or should I continue to lean into this?

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