Dating a much younger girl... can it work?

There is a young lady who works at a Starbucks hut that I go to every morning. We've chatted on several occasions and I'm really starting to like her personality. She is very beautiful and gorgeous. The problem is she is only 25 and I am 53. I want to ask her out on a date, but I feel like this would creep her out. I have a daughter who is 20, and this could also make things uncomfortable for her.

I've been divorced for 7 years and have been longing for a relationship again. I feel having this young girl in my life would rid my depression and make me happy again. That's if she accepts my offer to go on a date (s).

Should I try and ask her out, or should I go for a girl closer to my age?


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Most Helpful Girl

  • Closer to your age is better
    Plus she's working every time you go to Starbucks aka she's just being friendly to the customers as one is
    Plus you said your daughter is 20
    Don't think she'd feel comfortable for her dad to date a woam only 5 years older than her so that can cause some issues with your daughter and yourself

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    • Yes, I feel like the relationship between my daughter and I could be ruined. Could there be a way to find out if my daughter would accept such an age gap? I really don't want my daughter to turn bitter and angry towards me.

      I do like to keep my dating range to 35+ but I've kind of fallen for this particular girl. maybe I would be turned down and seen as a creepy old man, but it wouldn't hurt to pursue this young lady I assume?

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    • You could also ask yourself something, how would you feel if your daughter dated with a 50 year old man?

    • @DarkEmblem he's got a point xD

Most Helpful Guy

  • She's nice to you because you're an old man to her, leave her alone

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    • This is what I thought at first. She's young and I would be seen as a creepy old man. But I've been thinking about this, and we might be compatible in a few ways. We both have some interesting conversations, but I can still tell she doesn't get some of my jokes.

    • Leave the young girl alone

What Girls Said 6

  • I mean, you can try it but you probably won't have a lot in common.

    What's most concerning to me is that you want to use another person as a crutch to pull you out of a depression. This is not a healthy attitude. Putting all of your emotional reliance on one person will just create distress for you and animosity for them in the long run as it puts a lot of pressure on them. You really ought to focus on being happy within yourself before trying to make a relationship work with anyone else, let alone using someone to make you feel better.

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  • No hurt in asking her out. But, be prepared for her to turn you down.

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    • Would she turn me down because I'm much older? I guess that makes sense.

    • Yes. Her being nice and willing to chat with you doesn't equate to having interest. But it wouldn't hurt to let her know you're interested. Nothing to lose, right?

  • No. Not a good idea. I promise you, that's a bad idea in every way.

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    • How so? I'm curious to know because you're her age and I think it would give me so insight on why it might not be a good idea.

    • I don't know of anyone my age that is interested in men that much older for reasons other than money or influence.

  • Does she seem to be romantically interested? Is she single? What's her opinion on big age gaps? I would ask her these things before asking her out on a date. I personally think you should try for a girl closer to your age. But, if she's for it, then what could it hurt?

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    • I'm not sure if she's romantically interested, but she acts differently towards me compared to her other customers. I believe she is single though, I've never heard her mention a boyfriend. I would appreciate even a one night stand with this young woman, even if she thinks I'm too old for her. I need to drop hints too.

    • Dropping hints, and asking whether she's still in a relationship or not. Just be cautious going about it.

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  • I wouldn't ask her out she is probably just being friendly

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What Guys Said 4

  • I know how you feel. They are like a breath of fresh air! But I don't think you should ask her unless she is no-mistake bluntly obviously flirting with you. Otherwise are you setting yourself up automatic rejection and embarrassment from now on when ever you see her.

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    • True, and yes, young women are a breath of fresh air. :) It's hard to tell if she's ever flirted with me and it may just be her treating me like a customer. Should I ask her opinion on age gaps first?

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    • That is a great idea. It's like dropping a hint and indirectly asking her out. We've had some good talk, but I can see where she doesn't understand some of my jokes. If she accepted my offer, what do girls her age like to talk about?

    • They are all different, which is good, so there is no stereotyping. For sure you need to be familiar with texting, Twitter, instagram and all that stuff. After that, just talk to her try to get to know her and see what she is into. Being totally different isn't bad either. Dating someone who is exactly the same as you would be boring, right? You want someone different to keep things interesting. This gives each other a chance to learn new things and broaden their horizons. Some younger women do like older guys because guys their age are still punks and want to fuck around all the time and party. Older guys are more mature and have their lives together which is much more appealing. I do have to warn you though, she may not want an older guy because she probably wants children one day and may feel that won't be possible with you since most older guys are not interested in starting a family again.

  • Ideally, you should be going for women closer to your age.

    If you do want to give it a try with her, make sure you approach her when she is off-duty. Otherwise, it can get really awkward for her.

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    • Yes, I feel like women under 35 are too young for me at this point. But this specific girl brightens my day every morning I see her. I've kind of fallen for her.

      I feel it will get awkward even approaching her off-duty to ask her out, because she's young enough to be my daughter and she'll think of me as some pervy old man.

    • Well... some women actually prefer older men. And if you make it clear that you are just considering her as an individual you'd like to date, and it's not due to her age, she probably won't think that you're pervy. Give it a try!

  • Why can't it work? What is there to lose by trying? When I'm your age, I wouldn't feel any shame in approaching a younger girl who I'm attracted to and have chemistry with.

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  • Dude--you only live once, so give it a shot! Just realize that there's literally a 1% chance or so that she says yes. So long as you're totally cool with asking her out and her saying "no" (and you really should be) then go ahead and go for it.

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