Dating : So, I’m kinda dating a woman who is 10 years older than me (Me: m21, her: f31). What should I do, where should I go with this?

Dating : So, I’m kinda dating a woman who is 10 years older than me (Me: m21, her: f31). What should I do, where should I go with this?

Hey guys. So I’m saying « kinda » because its nothing big at the moment- we’ve been on a couple simple dates, like lunch, etc. . We hang out when our work schedules allow it, and when we’re not in person we text every day. There’s also been a good bit of flirting from both sides.

She’s a great person. She’s funny, interesting, humble, and just an all around kind-hearted person, which are traits that seemed hard to come by when i was looking in my own age group. She’s quite attractive too- I honestly thought she was around 23-24 when i first met her, i was a little surprised to learn she was in fact 31. Despite the age gap, we do have alot in common. I guess we’re kind of both at the same place in life too- we both still live with our parents, and work basic minimum wage jobs. She lives with hers again because she fell on hard times a couple of years back. I guess in a way, we’re both trying to find our place in the world still, even though she is significantly older. My mom, well, isn’t too happy that a 31 y/o woman is « after her 21 y/o boy » but, yknow, that happens with age gaps. Her mom is in a similar position, although according to my date, her mom likes me so far, but is also skeptical about the age thing.

Alright alright ill get to the point. She seems to be very interested in me, and honestly, I’ve been growing more and more interested in her. My dad tells me that she seems to be waiting for me to make a move, and I kinda want to. I want to take this further, but, I’ll admit, I’m also kind of scared about the age thing. I guess I find her somewhat intimidating- obviously, she’s a fair bit wiser and more experienced than i am. Also, I fear that because of the age gap, things might not work out in the long run. Or, maybe I’m just overthinking.


So, what do you guys think I should do? I’m in a bit of a pickle here. If I were to try to move things further, how should I go about it? I know it sounds a bit weird for a 21 y/o guy to be dating a 31 y/o woman, but yknow, things happen i guess lol

What do you think?


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  1. Ask yourself this one question are you genuinely interested in her?

    If yes, take the ride on the journey. Why not enjoy the journey of the relationship regardless if it might fail one day? I mean that would technically be the same if she was 23-24 and the thrill of dating it could end at any time, right?

    You’re overthinking it too and I get that you’re immediate (I’m In a relationship with an older woman as well) but I can tell you this it doesn’t mean you can lead or be you in the relationship. Learn from her experience, wisdom, Nd enjoy her company.

    How should you go about it? Your both adults. Stop thinking about it as an age thing and more of a she is a woman interested in you type of way.

  2. Stop overthinking this and just make a move. She obviously is interested and you enjoy her company. So just go with the flow of life and stop worrying about a number that really doesn’t matter.


    Can you tell the future? I ask that because you don’t know if you are going to get hit by a bus or something tragic happen. I’m not trying to sound negative, I’m trying to open your eyes that life is too short to worry about a number and walk away from a person that you enjoy being around. If you can tell the future then you wouldn’t be on here and over thinking this. Go for it an just enjoy your time on earth. The sun will rise tomorrow but you’re not guaranteed anything from anyone. You’ll regret it and continue to wonder what it could have been if you walk away, especially because of a stupid number. If you were 17, or under age that would be totally different. but, you’re both adults who make their own choices on how to achieve happiness.

  3. Women live longer than men, so yall die together, at the same time at the ripe old age of 80&90. It dont matter in the long run! Shoot your shot and good luck man.

  4. There’s an unwritten rule I like to use when dating someone younger. Cut your age in half and add 7. So 31/2+7=22.5. So judging by this, you’re too young for her.

    However, you seem to have articulated your thoughts well here and it sounds like you’re thinking more maturely than the typical 21 y/o. So, I say go for it. My grandparents have been married 45 years and my grandma is 8 years older than my grandpa.

  5. Like the others said, do you like her? Is she someone you want a relationship with? That age Gap isn’t really a bid deal. Just go with it and see what happens 🙂

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