Can a 23 year old man date a woman around 40 years old?

here's an older women I’m interested in at my job, we are co-workers. She's thanks me a lot and one time she said, I'm an angel for always helping her at work. I got her phone number yesterday and she didn't ask any question about it and also hasn't mention a boyfriend or husband ever since I've been talking to her, but yesterday she told me she’s single because I asked her, if her husband helps her out around the house. After asking her that, she asked me, if I have a girlfriend. She only mentions her daughter and grandsons. She showed me pictures of her nephew and I told her I looked like that when I was little, but then told her I was just joking haha, she said, no you're handsome.

I asked her, if I look better with my glasses on or off and she said, that I look cute with them on. I didn’t expect that answer from her, it was nice. I don't care about her age, just our conversations and just having a great time with her at work, and being helpful. I would joke around with her and she would say, that I'm cute. She also gave me a hug because I told her that you can always let me know, if you need help.

We work in different departments at the store we work at. I don't know, if she knows that's I'm interested in her. It looks like she does because whenever I walk past her I would look bad at her and she would smile and I would smile back at her. I know she’s older than me, but I would like to possibly go out with her. Do older women know that someone is interested in them?

Things look great, but I'm curious, how long should I talk to her before asking her out for coffee? I've been talking to her for about three weeks now. I really want to hang out with her and talk to her outside of work. I feel like I can connect with her. She doesn't think I'm annoying because I ask her, if she needs help and she doesn't think that at all. I asked her, just to be sure. Her daughter is 30 years old from what she told me. She lives with her daughter, I believe.

Updates:
hrough a text message she told me, that no one has ever been this kind to her in a long long time. Also, she didn’t give me an exact age number because she asked me how old I was and I then ask her the same question, but she said, she’s around forty years old. My main question is, when is it a good time to ask her out for coffee? I’ve been talking to her for four weeks now.

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Most Helpful Girl

  • well, if her daughter is 30, she has to be at least 45 (in the case she had her as early as 15 years old) but more likely she is older than 45.

    Anyway, there is absolutely no reason why you 2 dating would be illegal. both are adults and can do whatever the fuck you please.

    She might know you like her, but probably expects a "friendly" sort of connection. My best bet is, she will be very surprised if you ask her out. I think she might be interested in you, because what other reason might there be to not wanting to tell you her exact age... Go for it man. Today, tomorrow. Next time you talk to her, just casually ask her if she would go for coffee with you. that's it.

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Most Helpful Guy

  • In answer to the first part of your question, she probably does know you are interested. Once women have children or pass thirty their ability to recognise signs of interest from a man doesn't diminish. They may doubt themselves more, especially as you are significantly younger than her, but she will have noticed the signs even if she isn't certain what conclusion to draw from them.

    As to the second part of your question, that is more tricky to answer. She could do, but equally she may look at you as someone her daughter's age so she relates to you differently. I'm afraid that if you want to find out you may have to dig a little deeper about the kind of guys she likes to date or, and this is the risky part, just ask her out. It doesn't need to be too heavy but you do need to be clear that you are asking her out, don't invite others along, don't say 'just as friends, of course', after you have asked her to dispel any awkward moment that may occur, and do be prepared that she may say no. I would always try to ask her out privately when no one else was about to eliminate any other pressures on her at that moment.

    A rejection could come in many forms but it is always worth remembering that if she was interested she would find the time, 'being busy at the moment' is a 'no' and you need to respect that. If it goes that way then try to carry on as you are with her, things may change as she gets to know you better, they may not, but you mustn't get hung up on it. If she says 'yes', then have fun and I hope it goes well for you.

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What Girls Said 29

  • It sounds like she just really sees you as a charming young polite man, but nothing that indicates she's interested in you. I think because you're close in age to someone who could be her son she might not be that interested.. But I don't know her so I can't really say.

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  • Ask this woman to coffee already, what are you waiting for? Lol, she seems interested right? Test it out, don't be shy ;)

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  • My older brother (13 mos older) had a thing with an older woman for a while. Without knowing the details, I think it was because their sexual peaks matched up. My mom wasn't too happy about it but he sure seemed to enjoy himself. Lol.

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    • Thanks for sharing that, I'll keep you updated. I'll feel a lot better now. I'm going to see her tomorrow, so wish me luck! Again, thanks! :)

    • Thanks for all the help, I really appreciate it! :) These last couple of days, I've been getting to know her more and just talk to her because I want to know, if I'm interested in her and I am. I've been helping her out at my work still and she's thanks me a lot and one time she said, I'm an angel. I got her phone number today and she didn't ask any question about it and also hasn't mention a boyfriend or husband. She only mentions her daughter. She showed me pictures of her nephew and I told her I looked like that when I was little, but then told her I was just joking, she laughed and said that I'm handsome, which was nice of her to say. She's a lot older than me, but I think she good looking. I don't care about her age, just our conversations and just having a great time with her at work, and being helpful. I would joke around with her and she would say, that I'm cute. I don't know, if she knows that's I'm interested in her. Do older women know that someone is interested in them?

    • I would imagine on some level she does but societal issues may subconsciously prevent her from acknowledging it. You may need to be overt in your attractions.

  • You're a legal adult, it isn't illegal.

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  • ahh that is so cute. You have a crush one someone older. But here is one thing. Unlike men and younger girls, older women aren't attracted to younger guys. They might think they are attractive or even handsome but always see you as a kid. That is so sweet though!

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  • You posted this already.

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    • Haha I'm just saying! Also because I can't find the last one to copy and paste my answer to this lol. i just say don't get your hopes up, because she might just think you're a nice guy. I'm not getting any signs that she's interested.

    • Oh, okay... :(

  • Of course it isn't, you're 23

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  • I'm saying maybe, because I know some people like others who are younger than them but trying to find a significant other through work isn't ideal... but good luck!

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  • She seems to be very friendly with you, ask her for a coffee, it can't hurt and it's not outright asking her on a date lol

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  • why would it be illegal?

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    • I'm just curious, since she's older than me. How should I bring up having coffee with her and when should I ask her out for coffee? I've been talking to her for about four weeks now. The help is appreciated! :)

  • Do whatever you want.

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    • Thanks for your answer, I appreciate it. :) When should I ask her out for a day out for coffee? I want to take things slow and not rush it.

    • I got her phone number and she didn't say I couldn't have it since we don't know each other outside of work.

    • #Asker ya no worries! That's fantastic that you got her number. Yes go out for coffee! or even try a laid back dinner. Or whatever you think she's going to like. She probably have you her number Becuase she's comfortable with you ☺️

  • It's not illegal man, as long as you're both over 18 it's fine. If you like her, go for it ask her out!

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  • That's legal you are over 18 your fine.

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    • Okay, thanks for your answer! How should I bring up having coffee with her and when should I ask her out for coffee? I've been talking to her for about four weeks now. The help is appreciated! :)

  • illegal? No

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  • Yes it is possible

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    • Thanks for your answer, I appreciate it. :) When should I ask her out for a day out for coffee? I want to take things slow and not rush it.

    • I got her phone number and she didn't say I couldn't have it since we don't know each other outside of work.

  • Yeah totally possible. I know the writer L. K. Hamilton married a younger man after her divorce.

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  • DEFNETLY NOT WRONG. I think everyones goal in life should be to be happy not hurting other people. If you loving an older woman makes you happy and you're not hurting anyone then go for it. :) You deserve what you want and nothing less than that. :)

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    • Wow, thanks for your answer! I feel a lot better knowing that. I'll keep you updated. I see her tomorrow, so wish me luck! Again, thanks! :)

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    • Thanks for all the help, I really appreciate it! :) These last couple of days, I've been getting to know her more and just talk to her because I want to know, if I'm interested in her and I am. I've been helping her out at my work still and she's thanks me a lot and one time she said, I'm an angel. I got her phone number today and she didn't ask any question about it and also hasn't mention a boyfriend or husband. She only mentions her daughter. She showed me pictures of her nephew and I told her I looked like that when I was little, but then told her I was just joking, she laughed and said that I'm handsome, which was nice of her to say. She's a lot older than me, but I think she good looking. I don't care about her age, just our conversations and just having a great time with her at work, and being helpful. I would joke around with her and she would say, that I'm cute. I don't know, if she knows that's I'm interested in her. Do older women know that someone is interested in them?

    • Well they have a lot experience... so she probably knows and she hasn't pushed you away yet. however I would try not to compare "yourself" to her nephews because you are just reminded her that you're younger. So for me i would say keep going. if she hans't backed out she probably has feelings as well.

  • No. We older women are extremely dense about this stuff. You have to probably be direct.

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  • Heck no, my boyfriend is 20. Age is just a number.

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  • You already asked this before. Dont eat where you shit. Dating coworkers is NEVER a good idea. Plus a woman that age is at a different stage in her life. Will you guys be able to synchronize with that stage? You are barely starting your life out.

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    • I did earlier today, twice lol.

      @SucessfulPerson09 it's cool if you have a question but it really sounds like you're fishing for answers and validation/encouragement to ask her out. You only sound super excited when someone says to go for it. If you really want to ask her out them go for it. You're not gonna listen to us lol. All I'm saying is don't be disappointed if she says no, she has many reasons to. And if she says yes then good for you too, just be aware of the difficulties that come with that large of an age gap.

  • She's just being a sweetheart bruh, but she seems like a nice person. y'all can be friends, but she ain't a cougar, like she's not aggresive or anything, just a nice lady with a family of her own.

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    • Thanks for your answer, but I feel like I have a good connection with her. :) She doesn't have a boyfriend or husband.

  • No it's not illegal.

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  • Why would you think its illegal. You're not underage you're a grown ass man.

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  • Don't eat where you shit.. It's never good to date coworkers. But no, it's not illegal to date a woman that age.

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  • Nope, its legal

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    • Okay, thanks for your answer! How should I bring up having coffee with her and when should I ask her out for coffee? I've been talking to her for about four weeks now. The help is appreciated! :)

  • Can't help who you like. I'm an older girl who has a thing for a younger guy. Age doesn't matter as long as you're both comfortable with it. If you make it a big deal then that's when it becomes a problem. Talk to her about it. I'm sure she doesn't mind that you're younger.
    And just to let know people will talk about the age difference, but it isn't their choice remember it's yours

    Good luck

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    • Thanks for sharing that, I'll keep you updated. I'll feel a lot better now. I'm going to see her tomorrow, so wish me luck! Again, thanks! :)

    • Thanks for all the help, I really appreciate it! :) These last couple of days, I've been getting to know her more and just talk to her because I want to know, if I'm interested in her and I am. I've been helping her out at my work still and she's thanks me a lot and one time she said, I'm an angel. I got her phone number today and she didn't ask any question about it and also hasn't mention a boyfriend or husband. She only mentions her daughter. She showed me pictures of her nephew and I told her I looked like that when I was little, but then told her I was just joking, she laughed and said that I'm handsome, which was nice of her to say. She's a lot older than me, but I think she good looking. I don't care about her age, just our conversations and just having a great time with her at work, and being helpful. I would joke around with her and she would say, that I'm cute. I don't know, if she knows that's I'm interested in her. Do older women know that someone is interested in them?

What Guys Said 34

  • 1. She is much older than you so she has much more experience in relationships. Of course she knows that you are interested.

    2. If her daughter is 30, then this woman is probably at east 46 or 47 years old.

    3. Older women can be very helpful to a younger guy. You may not have much chance for a LTR but you might have some good times together. Just make sure that you hold on to your heart and don't get too wrapped up in her too soon.

    4. Invite a group of co-workers to a happy hour after work and then invite her to join you. It is a non-threatening invitation; if she wants to spend time with you, she will accept and hope to eventually be alone with you but she can always leave if she does not want to be alone with you.

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  • also 3 weeks is a long freaking time. if this was a younger girl you probably would've been friendzoned by now. also, i don't recommend shitting where you eat unless you absolutely know you can handle your emotions because TBH cougars don't usually look for LTRs with young guys they just want the experience and validation a young guy gives them. hope it works out for you

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  • I'm sure she is very aware of what she is doing, you just need to make sure she is actually attracted to you as a person, and not that she is actually just attracted to younger guys (as like a fetish). Just like some older men are attracted to younger girls, it's more of a fetish thing, and often used as a confidence booster for the older party involved.
    Basically it makes her feel good about her self to know she can still attract a guy in his twenties, instead of her being attracted to you specifically regardless of your age.
    If your ok with just being an ego booster to her, than go for it. But if your looking for something deeper than sex, she may not be the right call for you. Good luck and make sure you value yourself.

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  • I'd just ask and see how it goes. She may just being friendly, she may be interested. Most 40yr olds I meet are not interestd in 23 year olds. but who knows.

    Either way, it can be a great relationship, I had great older female friends that I decided not to take any further... and that was a very wise move on my part. your scenario may be different.

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    • Thanks for your answer, I appreciate it. :) When should I ask her out for a day out for coffee? I want to take things slow and not rush it.

    • I got her phone number and she didn't say I couldn't have it since we don't know each other outside of work.

    • When, you mean what day, or how?
      Make it fun. find a coffee shop that has live music you'd enjoy and she might as well. Send her a text or when you see her in passing..."hey reminds me, there is this band playing at a coffee shop on Friday night I'm gonna check out. Would you like to join me, thought it would be fun." something like that, put in your own words.

      that way it is presented as you are doing something anyway and will have fun no matter what (no obligation), and you were thinking of her (always good) and that it would be fun for her as well (girls like fun). She'll either bite or brush you off. if she brushes you off... I need to hear the brushoff to judge.

  • No. Why would it be illegal? It's possible your company may frown upon dating a coworker, but not illegal.

    Ask her out next time you see her if you want to. Why wait? And don't bring up her age. You both already know she's older, so if you don't want to date an older woman than don't ask her out. If you're ok with that then just ask her out and treat her like any other woman.

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    • Okay, thanks for your answer! :) Are these signs that she might be possibly interested in me?

  • you're a legal adult so aside from a relationship with an animal or a blood relative (in most places) you are fine to have a relationship with whomever you want

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  • If you want to get to know her better , feel free to message me. Older women have always been my goal and I may be able to help you on this

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    • Thanks, I appreciate your help! :) From what I told you, does she know that I'm interested in her?

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    • Yes. Start with a simple coffee. Don't go in with a pre conceived notion of anything beyond the coffee. Don't allow your self to talk about anything that will give off the vibe of immiturity. Be very attentive and interact in dialogue that you see interests her. If the coffee meeting goes well ask before parting ways if she would like to have dinner sometime

    • Okay, I'll ask her the next time I see her. :) She told me last night through text that she enjoys my company and no one has been this kind to her in a long long time.

  • She's wanting you to ask her out. Get this over with

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    • Thanks for your answer, I appreciate it. :) When should I ask her out for a day out for coffee? I want to take things slow and not rush it.

    • I got her phone number and she didn't say I couldn't have it since we don't know each other outside of work.

    • I would make the call. If it fails, you can always avoid her since you work in different departments. Remember what Ben Franklin wrote, and good luck!

  • Its something very different but not a problem at all

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    • Okay, thanks for your answer. I'll keep you updated. Again, thanks! :)

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    • Okay, thanks! Again, thanks for all the help! :)

    • Your very welcome

  • Your life and freedom. No one is stopping you. Just follow your heart. Some cougars are hot. I saw one today wearing leather pants.

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  • Go get your cougar

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  • I can't tell if you're actually asking this question or rather looking for a soundboard to let your thoughts run wild... I'm hoping it's the later.

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    • I'm asking questions...

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    • I'll go where I please and say what I wish. If you have a problem with that then click on my user name, look at the top right hand side of my profile, click on the little 'X' to prevent it.

      However, if you're going to pretend to be naive and cat fish responses, deal with the ensuing responses. They're unavoidable.

    • I'm not the one with a problem.

  • I like older woman, I would have no problem dating 30-40 year old woman, given that I'm only 23. Whatever make one happy really, there is nothing else that should matter.

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    • It's great knowing that, thanks! I'll update you tomorrow. :)

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    • Sounds good man. Woman are generally aware when men are interested in them, but you got to make this fact solid, just so you don't get friend zoned. Outside of what I already said I can't offer much more advice as I'm just a pessimistic twat with a computer who's answer are based on logic. But best of luck mate.

    • Thanks, I appreciate it though! :)

  • Wait... she's around 40 with a 30 year old daughter? And she has grandkids? The math just isn't adding up for me.

    Regardless, go for it and see what happens.

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  • both of u are grown up but make sure she has feelings for u other than that no problem at all

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    • You're right, thanks for your answer. I'll keep you updated. Thanks again! :)

    • Thanks for all the help, I really appreciate it! :) These last couple of days, I've been getting to know her more and just talk to her because I want to know, if I'm interested in her and I am. I've been helping her out at my work still and she's thanks me a lot and one time she said, I'm an angel. I got her phone number today and she didn't ask any question about it and also hasn't mention a boyfriend or husband. She only mentions her daughter. She showed me pictures of her nephew and I told her I looked like that when I was little, but then told her I was just joking, she laughed and said that I'm handsome, which was nice of her to say. She's a lot older than me, but I think she good looking. I don't care about her age, just our conversations and just having a great time with her at work, and being helpful. I would joke around with her and she would say, that I'm cute. I don't know, if she knows that's I'm interested in her. Do older women know that someone is interested in them?

    • Good for u mate ! And yes older women do know since they have experienced a lot in life so hope sje is interested :)

  • Yeah go get them cougar I mean tiger XD

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  • not at all. You are two adults.

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    • Thanks for your answer, I appreciate it! I'll keep you updated! :)

    • Thanks for all the help, I really appreciate it! :) These last couple of days, I've been getting to know her more and just talk to her because I want to know, if I'm interested in her and I am. I've been helping her out at my work still and she's thanks me a lot and one time she said, I'm an angel. I got her phone number today and she didn't ask any question about it and also hasn't mention a boyfriend or husband. She only mentions her daughter. She showed me pictures of her nephew and I told her I looked like that when I was little, but then told her I was just joking, she laughed and said that I'm handsome, which was nice of her to say. She's a lot older than me, but I think she good looking. I don't care about her age, just our conversations and just having a great time with her at work, and being helpful. I would joke around with her and she would say, that I'm cute. I don't know, if she knows that's I'm interested in her. Do older women know that someone is interested in them?

    • sounds good then. hopefully it works out

  • No it's not illegal 😊

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  • It's legal, and guys date younger women. I say it's ok.

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  • No, but it's illegal if you date girls who are children.

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    • Okay, thanks for your answer! How should I bring up having coffee with her and when should I ask her out for coffee? I've been talking to her for about four weeks now. The help is appreciated! :)

  • You just asked this. Lol. But again, it doesn't hurt to try BUT be careful as it could lead to some consequences at work.

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  • Um... You back at it mate? I swear I seen this question before... Dejavu

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  • Go for it, and if you crash and burn you learned something new

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    • Thanks for your answer, I appreciate it. :) When should I ask her out for a day out for coffee? I want to take things slow and not rush it.

    • I got her phone number and she didn't say I couldn't have it since we don't know each other outside of work.

  • Yes it is possible. I'm dating a woman who is 16 years older than me.

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  • you realise in the eyes of the young you're both old now right? one cares, bump uglies and have fun

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  • I'm 23 and just had a fling with a 45 year old. Though, I'd be weary if you two work together. It could cause problems for both of you.

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  • I can give an opinion, but judging from your responses in the comments and human nature you already have everyrhing planned.

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  • nothing is illegal

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  • Not yet but as it currently it's a crime for a guy 52 to look at a female is she's 18. So it won't be long before the legal age for women hits 41. Better make your move now before it happens.

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    • Okay, thanks for your answer! How should I bring up having coffee with her and when should I ask her out for coffee? I've been talking to her for about four weeks now. The help is appreciated! :)

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    • Okay, I'll try that, thanks! Wish me luck! :)

    • You got it good luck to you!

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