I'm an older man but I want to ask out a younger woman

[Phillip R]

I'm in my mid-40s, but I have come across a young lady that is a genuinely sweet and kind hearted woman and I really just find that so attractive. I'm not exactly sure what her age is, but we have had passing conversations and I really would like to get to know her better. My issue is that I think she is in her early 20s. I don't want to be a creep. Should I ask her out or just let this pass?

[Coily]

Chat her up, no harm in getting to know someone. If she’s interested good, if not you at least never have to ask what if. 
With that age gap expect for things to not work, but some people just click.

I know there will be naysayers on here, but if they get insulting or attributing mal intent, ignore them. 

[Capricorn3]

1 hour ago, Coily said:

With that age gap expect for things to not work, but some people just click.

I agree.  You're old enough to be her father.  I guess it would all come down to how she feels and, of course, what her actual age is.  Who knows, even if you did date for a while, it's highly unlikely it will turn into a long term relationship (imo).  She's on a completely different page to you currently, and maturity levels are at odds too, etc. Maybe she already has a boyfriend.  Lots to think about.

[Kwothe28]

I think its very unlikely that something could happen. No offence, but most of the couples with that age difference include older rich man and young golddigger. I mean Chris Evans just married some woman who is 17 years younger. But he is also rich and is, well, Captain America. If we are talking some more grounded scenarios, things like that rarely happen. Firstly, because 20 year olds are usually attracted by other 20 year olds. And secondly, because age gap makes a big difference. For example young 20 year old would like to go noisy clubs as her friends usually do. Most 40 year olds dont enjoy that and find it a nuisance. Its very hard to connect at all due to age difference. 

But, if you want to try I see no harm in exchanging a few words with her and sseeing if she is interested. 20+ is adult age after all so its not forbidden.

[MissCanuck]

You could ask her out but keep your expectations very low. 

You're at totally different points in your lives and it's just not that realistic a prospect. She's just learning who she is as an adult, what she wants in life, and so on. You (presumably) are well past that stage. This doesn't generally bode well for a relationship. So while there are no moral issues, there are a number of other variables that render a true romantic connection not that likely. 

[TacticalLinguine]

Encourage you to look the other way. Most women, myself included, end up feeling quite "icky" about the older men that made moves when they were young adults. Sorry to be blunt. But it is what it is. 

[MrMan1983]

4 hours ago, Phillip R said:

and I really just find that so attractive.

The question is, are there tell tale signs she finds you attractive in that way or just a bit of polite convo? I've recently been involved (nothing serious) with a mid 20's girl at the age of 40 but it was pretty obvious she was interested at least in a more than mates way. Might be worth finding out just how young she is too if you're mid 40s.

[NighttimeNightmare]

1 hour ago, TacticalLinguine said:

Encourage you to look the other way. Most women, myself included, end up feeling quite "icky" about the older men that made moves when they were young adults. Sorry to be blunt. But it is what it is. 

Yup. I’m ok with age gaps when the younger party is well, older.

 

there’s an interesting study that was conducted that essentially showed how enthusiastic some young women were about dating men much older. They felt grown, mature, chosen, etc. However, when those young women grew up and were now the age of the men who pursued them, they were disgusted and felt taken advantage of. 

[Wiseman2]

6 hours ago, Phillip R said:

 we have had passing conversations and I really would like to get to know her better. 

How do you know each other? Are you a customer where she works? 

There's no rush to ask her out. Hitting on women out of context can come across as "creepy" at any age. 

[Batya33]

How do you know her? What about her actions are kind hearted? Are you a sweet and kindhearted person? I find your description of her kind of childlike - sort of a focus on how sweet/cute she is and then you swoop in as the older sophisticated man?

[Jibralta]

7 hours ago, Phillip R said:

My issue is that I think she is in her early 20s.

Ask her how old she is. She might be older than you think. I got carded routinely--almost without exception--until I was 35. 

[boltnrun]

A woman I know married a much, much older man. She is a very attractive and accomplished woman in her own right so she didn't need his money. But yes, the man she married is quite wealthy. 20-ish years in they are still happily married and have two children. 

When I was in my mid 20s I was quite attracted to a man in his 40s.

How did you "come across" this woman? (Please don't tell us she's a barista at the coffee shop you frequent!) What indications has this woman given you that she might be interested in a date with you?  

[itsallgrand]

How do you know her? Will she be in a position where she has to interact with you again ?

I mean, yes, you do run the risk of coming off inappropriate. You have to weigh potential consequences and decide if it is worth it.

Some things to think about you may not have considered are how it may come back around later. You'd be amazed what women are observing and how word travels. To give an example, many years ago at a workplace when I was starting the coworkers there alerted me immediately to which customers had asked people there out. They had all this information on them you wouldn't think. Another example, there are men I've never even actually met in my life who family members and others I know have dished about, red flagging them if I ever come across them! 

Point is, it's not just her watching. You risk alienating/making a poor impression on others who you may wish to date or have to interact with later too.

 

[smackie9]

You will have very little to nothing in common....so there is no point. 

[rainbowsandroses]

11 hours ago, Phillip R said:

My issue is that I think she is in her early 20s.

What makes you think that? I wouldn't go by looks, many women AND men look a lot younger than their chron age.

I know of many including myself, and my dad who was 74 when he passed away, looked 20, even 25 years younger.  I'm not exaggerating.

So as @Coilysuggested, chat her up and get to know more.  If age comes up, be truthful.  

If she is in her 20s, I know large age gap couples where it works, it depends on many things -  maturity level, life experiences, how well you vibe together, the chemistry betwen both of you.

Don't assume because she's in her 20s (if she is in fact in her 20s) she won't have the maturity level for a man in his 40s, again it depends.

And a woman can be a golddigger at any age. 30s, 40s, 50s and up. 

There is a saying I believe in - "You miss 100% of the shots you don't take."

Good luck and let us know what happens!

[lostandhurt]

I just recently spent time with several women that are at least half my age or younger while doing a fundraiser and one in particular was through my eyes flirty with me.  Do I think she is attractive?  YES in all areas but will I pursue anything?  No I will not because for one thing I find a lot of women very attractive that talk to me and are nice and pleasant but I know my place.  I have been down this road with a young woman half my age once that asked for my number and we did date briefly but I ended it because it did not feel right.

 If you have only talked in passing then I am guessing this is mostly in your head and she is not into you.  I agree you need to chat her up more and get a feel for her interest level BEFORE you ask her out.

 I will tell you that women of this age feel safe with older guys so they are more friendly and open since they don't worry that being nice to a guy your age will lead to him trying to ask them out.  Now a young man they are not attracted to will be treated more coldly to avoid having to shut them down later.

 Good luck

 Lost

[NighttimeNightmare]

3 hours ago, lostandhurt said:

 I will tell you that women of this age feel safe with older guys so they are more friendly and open since they don't worry that being nice to a guy your age will lead to him trying to ask them out

This is so true and also how many older men end up betraying that innocent trust and taking advantage of the younger party, often sexually  

 

I have an older friend in his 60s who is a bonafide pervert.  He looks like “santa” and younger women flock to him because he seems safe and fatherly. Eventually they end up at his house sleeping with him. I tell him, “you know they’re only running to you because they need help and see you as safe.”  He knows it, and uses it to get what he wants.  They almost always end up sleeping with him in exchange for room & board, money. Etc.

 

so yes, @Phillip R  , everyone is cheering this on but I’m sorry, you do and will look like a creep because at age 22 (-/+) that individual is trying to determine who they are as a person and navigate life socially, financially, emotionally, etc. They need peers and solid parental figures to do this and help evolve them into functional adults.  At her age, you resemble a father figure, so why do you want to sleep with her?  It even seems to feel wrong, or ‘off,’ to you because you mentioned it and used the word “creep”

 

I will be the odd man out here. 

[waffle]

7 hours ago, rainbowsandroses said:

What makes you think that? I wouldn't go by looks, many women AND men look a lot younger than their chron age.

And many look a lot older.  Not at all unusual for a man to think a woman is in her early 20s and she's 14.  Then he ends up on the sex offender registry.  Be smart, assume nothing.  What's wrong with women your own age?

[boltnrun]

18 minutes ago, waffle said:

Not at all unusual for a man to think a woman is in her early 20s and she's 14.

Very true. When I was in high school my friends and I had one of our friends buy us beer all the time because she looked 22 but was only 15. And I looked 17 when I was 25. 

I'm still curious to know where the OP "came across" this young woman. 

[SooSad33]

Mid 40's and early 20's?  Nope.

I think it's best you let this 'crush' die out and move on. 

You do realize you are old enough to be her father?  I could & would NEVER date a guy my own kids age!

Plus, there's such a large age gap, in time you realize, other than 'looks', what else do we have in common?

Anyways, is just too much imo.  It's a no.