Crushing on a woman younger than me. Should I tell her?

January 10, 2015

Hello to all! In somewhat of what I consider a crazy, but fairly normal predicament. I'm a 33 year old male, who has been crushing on one of my sister's friends for a couple of years now. The young lady is 23 years old, in grad school, very smart, and extremely beautiful in my opinion. There's seldom a day that passes when she doesn't cross my mind a bit.

I've always thought she was attractive, but it all started a couple of years ago when she spent some time with our family during the holidays. I had the chance to interact with her a bit (not too much), and she's always been nice and friendly towards me whenever she has seen me. We even have some mutual family members (same cousins), although she is I aren't related. I added her as a friend on Facebook last year, but we haven't had much interaction on there.

I saw her several times during the recent holidays, while she was hanging out with my sister. Before she left to go back to grad school, I was finally able to get my first ever hug from her. Over the past year and a half, several of my guy friends and even a few female friends told me that I should tell her how I feel about her. However, I haven't said anything because of the age gap between us. I'm mainly concerned that she would think I'm some old creeper that's targeting her, which is not what I am doing at all. Believe me, I wish I didn't have this crush on her, or I wish that at least I was younger.

I know there is little to no chance that she and I could ever be together, and I'm cool with that as long as she and I could at least remain acquaintances. However, I wish I had the confidence to tell her how I feel for my own personal sanity. I even told my sister last year, and she told me that she could help put me out there, but I told her not to say anything. I don't believe she has, but you never know.

So would you all tell her if you were in my position? I do know that when they were in high school that she told my sister that I was handsome. However, that doesn't count since she was underage at the time. Also, where she attends grad school is in a city that I have family in and visit quite a bit. I would've been said something to her if I wasn't concerned with it making things awkward for her if she came around again. It just sucks looking at her sometimes wondering what if! Thanks.

January 10, 2015

Normally I'd say to leave it because she is a friend of your sister which could make things very awkward for her having to divide time between you and your sister. However, at this point you actually seem to have your sister's blessing so she seems supportive. Maybe best thing you can do is, still don't let your sister say anything. But maybe see if your sister and her friend would be down for a night out or something between the three of you, maybe grab some dinner or coffee, whatever. This way you can get a chance to talk to her and get to know her, see if she might be feeling the same, or she might not. And its with zero pressure because its just a night out for casual fun. I'd say the age difference is really not that far, so it would be ok to date her. But it just depends on how receptive she is. I hope this helps.

January 10, 2015

Shared relatives, 10 year age gap, your sister's friend, long distance, have known for 2 years already... this could and likely would turn into an awkward situation. Not all crushes are worth the risk. I definitely wouldn't just tell her flat out that I have a crush on her. It is always best to just ask them out rather than to start confessing. It takes a lot out of it.

I wouldn't approach this woman but if the desire burns in you so much to do so, just ask her out to a fun, low-pressure event.

January 10, 2015

Normally I'd say to leave it because she is a friend of your sister which could make things very awkward for her having to divide time between you and your sister. However, at this point you actually seem to have your sister's blessing so she seems supportive. Maybe best thing you can do is, still don't let your sister say anything. But maybe see if your sister and her friend would be down for a night out or something between the three of you, maybe grab some dinner or coffee, whatever. This way you can get a chance to talk to her and get to know her, see if she might be feeling the same, or she might not. And its with zero pressure because its just a night out for casual fun. I'd say the age difference is really not that far, so it would be ok to date her. But it just depends on how receptive she is. I hope this helps.

^I really don't believe my sister has said anything to her. As far as the the night out thing, it likely won't happen since both my sister and her friend are both in college and seldom see each other.

Your advice is really helpful, and would be useful to me if the circumstance were different. Thank you for replying.

January 10, 2015

Shared relatives, 10 year age gap, your sister's friend, long distance, have known for 2 years already... this could and likely would turn into an awkward situation. Not all crushes are worth the risk. I definitely wouldn't just tell her flat out that I have a crush on her. It is always best to just ask them out rather than to start confessing. It takes a lot out of it.

I wouldn't approach this woman but if the desire burns in you so much to do so, just ask her out to a fun, low-pressure event.

^For me, reading your reply definitely puts the situation into perspective, and shows why I've been hesitant to tell her in the first place.

I never had any attentions on coming flat out and tell her that I liked her. Just wanted to let her know that I was interested in getting to know her better.

I'll likely stick to my guns and just not say anything. Although I'm interested in her, not all crushes are worth the risk like you mentioned. I suppose my feelings will pass over in time. Thanks for replying.

January 10, 2015

Good. Crushes are like fantasies, not all them needs to be acted on and it is often a good idea to not act on a good number of them.

January 10, 2015

Think you better tell your sister first and see what her reaction is. Say, "What would happen if I liked one of your friends?" Then take it from there. It might help to know how old the guys are your sister dates. Her friend may be doing the same. Best friends are often very similar in what they do.

In another two years, that union wouldn't have as many issues. 23 is pretty young and immature. The gap isn't that bad; it's how young she is as in just not being fully mature yet. But there are exceptions.

January 10, 2015

Think you better tell your sister first and see what her reaction is. Say, "What would happen if I liked one of your friends?" Then take it from there. It might help to know how old the guys are your sister dates. Her friend may be doing the same. Best friends are often very similar in what they do.

In another two years, that union wouldn't have as many issues. 23 is pretty young and immature. The gap isn't that bad; it's how young she is as in just not being fully mature yet. But there are exceptions.

^I already told my sister nearly two years ago that I kinda liked her friend. Not sure what age group of guys my sister goes for. To the best of my knowledge, my sister has yet to have a serious boyfriend.

I did overhear them talking recently though, and I believe I heard her friend say that she wouldn't date a guy over 40. Part of me was sitting there thinking that she wanted me to hear that.

Also, I want to add that several of my sister friends have had crushes on me in the past. I've never been interested in any of them except for this girl that started coming around a few years ago. My sister and I are very close, so I know many of the girls she hangs with.

I appreciate you words though as far as the age gap thing. I do realize that 23 is young and immature. However, her friend that I'm crushing on is very mature for her age. It's one of the qualities about her that I noticed and liked.

January 10, 2015

just go for it dude, step up your game and try to get closer to her in which ever way you can, just be semi indirect and if you feel she is not vibing it just back off and let it go that way it wont be too awkward in the future. You may end up always looking back and wondering what if... but if you do it what's the worst that could happen...a bit of awkwardness..... if your crushing as hard as you are seems worth it to me

January 10, 2015

I wonder though because usually best friends are similar in the men experience thing. If your sister hasn't been dating, I truly wonder if this 23 year old has any experience. She could be mature in some ways, like level-headed and completely immature otherwise. Probably time for a talk with the sister. How about "Would I be wasting my time asking _____ out?" She would surely know whether it was out of the question or not. Even if she just says, You could try, that means her friend didn't forbid her from encouraging you.

January 10, 2015

just go for it dude, step up your game and try to get closer to her in which ever way you can, just be semi indirect and if you feel she is not vibing it just back off and let it go that way it wont be too awkward in the future. You may end up always looking back and wondering what if... but if you do it what's the worst that could happen...a bit of awkwardness..... if your crushing as hard as you are seems worth it to me

^I hear ya brother, and you're right about the "what if" factor and stepping up my game. I was the one who initiated the hug a few days ago before she left. I never done that in the past. I'd rather tell her face to face than over Facebook though. Only thing with that is I don't know if and when I'll see her again. I can accept her telling me she's not interested if she isn't, but it would be hard for me to accept if she ignored me , which is something she can do easily if I send her a message. Thanks for the reply.

January 10, 2015

I wonder though because usually best friends are similar in the men experience thing. If your sister hasn't been dating, I truly wonder if this 23 year old has any experience. She could be mature in some ways, like level-headed and completely immature otherwise. Probably time for a talk with the sister. How about "Would I be wasting my time asking _____ out?" She would surely know whether it was out of the question or not. Even if she just says, You could try, that means her friend didn't forbid her from encouraging you.

^Well actually, she and my sister are not "best friends". They are actually classmates that graduated high school together. They only recently started hanging with one another a couple of years ago. I've pretty much known all of my sister best friends for years.

I'm not sure how much experience the girl I'm crushing on has with men. For awhile, I assumed that she liked girls to be honest. Like I said, all I know is that my sister told me when they were in high school that the girl I'm talking about said I was good looking. Again, that doesn't count in my book because she was a minor at the time.

You're probably right about me talking to my sister, which I may do next week. Last time I brought it up to my sister, which was last year, she encouraged me to message her, and that she could put me out there if I wanted her to.

January 10, 2015

^Well actually, she and my sister are not "best friends". They are actually classmates that graduated high school together. They only recently started hanging with one another a couple of years ago. I've pretty much known all of my sister best friends for years.

I'm not sure how much experience the girl I'm crushing on has with men. For awhile, I assumed that she liked girls to be honest.

Uh-oh -- sister not dating men -- only recently started hanging -- better be sure you're not stepping into the middle of a sister/sister situation here!

January 10, 2015

You'd be competing with dudes in her age-group (22-25) if you chose to pursue this. You may find her attractive but would she find you attractive? It depends on a few things but on average guys over 30 don't look as sharp as guys under 30.

January 10, 2015

You're not THAT much older than her lol. 33/23 isn't a huge deal IMO. If it was like 45/22 then you'd be getting into creeper territory, but even that gap still gets together sometimes.

Thing about older guy / younger gal situations is that you want to gauge interest very carefully before being at all overt. Some women don't respond very well if they perceive you as a 'mentor' age to speak, it can give seriously creepy/bad feels if they associate you with their biological father's age range, or even worse like a grandparent. It can be especially triggering if they had shall we say not-very-good male role models growing up.

However, if they see you as a peer, albeit a somewhat older peer, then it won't be anymore awkward than it normally would be if they're not interested, meaning there is no creeper-element in the mix.

I think that's the underlying psychological thing for a lot (but certainly not all) women when it comes to significantly older men. Since you're a decade apart, you're definitely not old enough (at least culturally) to be her father, so I think you're in the clear as far as older-creeper concerns.

If you were in your 40s then you'd be considered old enough to be her father and there'd be a much higher chance that she'd find your romantic (because let's face it, it's half sexual) interest unsettling, but even that sort of scenario you'd just need to gauge interest very carefully and make sure there are plenty of mutual interest green lights before going overt with it.

It definitely does happen that younger women find older men attractive / romantically appealing, but when they don't, it's disturbing / creepy for reason outlined above (IMO) so it all boils down to respectfully testing very shallow waters and waiting for green lights.

So in your case I personally wouldn't advise coming right out with it, but I agree with the idea of talking with your sister and getting her take on it. She knows this lass way better than you do, for sure, and could probably give you a decent square one indication of your chances and how awkward or not it would be.

January 10, 2015

Uh-oh -- sister not dating men -- only recently started hanging -- better be sure you're not stepping into the middle of a sister/sister situation here!

^Not likely lol, and believe me that has crossed my mind in the past. For one thing, my sister despises homosexuality. I've also met a couple of guys that she has went out with etc, she's just never been in a SERIOUS relationship.

January 10, 2015

You'd be competing with dudes in her age-group (22-25) if you chose to pursue this. You may find her attractive but would she find you attractive? It depends on a few things but on average guys over 30 don't look as sharp as guys under 30.

^Yea that is indeed true, and I've considered that. I've never had a problem attracting younger women, and even older ones. As a matter of fact, there was a 19 year old acquaintance of my sister that I met while visiting her at college that tried to convince my sister to pair us up.

Most people tell me that I don't look my age. A lot of times I easily get confused for a 25 year old. I don't drink, smoke, and I work out several times a week.

I don't know if she finds me attractive or not. It could be a toss up.

January 10, 2015

You're not THAT much older than her lol. 33/23 isn't a huge deal IMO. If it was like 45/22 then you'd be getting into creeper territory, but even that gap still gets together sometimes.

Thing about older guy / younger gal situations is that you want to gauge interest very carefully before being at all overt. Some women don't respond very well if they perceive you as a 'mentor' age to speak, it can give seriously creepy/bad feels if they associate you with their biological father's age range, or even worse like a grandparent. It can be especially triggering if they had shall we say not-very-good male role models growing up.

However, if they see you as a peer, albeit a somewhat older peer, then it won't be anymore awkward than it normally would be if they're not interested, meaning there is no creeper-element in the mix.

I think that's the underlying psychological thing for a lot (but certainly not all) women when it comes to significantly older men. Since you're a decade apart, you're definitely not old enough (at least culturally) to be her father, so I think you're in the clear as far as older-creeper concerns.

If you were in your 40s then you'd be considered old enough to be her father and there'd be a much higher chance that she'd find your romantic (because let's face it, it's half sexual) interest unsettling, but even that sort of scenario you'd just need to gauge interest very carefully and make sure there are plenty of mutual interest green lights before going overt with it.

It definitely does happen that younger women find older men attractive / romantically appealing, but when they don't, it's disturbing / creepy for reason outlined above (IMO) so it all boils down to respectfully testing very shallow waters and waiting for green lights.

So in your case I personally wouldn't advise coming right out with it, but I agree with the idea of talking with your sister and getting her take on it. She knows this lass way better than you do, for sure, and could probably give you a decent square one indication of your chances and how awkward or not it would be.

^This was a really good read. You make some excellent points. Thank you!

January 10, 2015

Your sister 'despises homosexuality?' Generally young people are more blase and open. That could mean she is a lesbian if she's in denial. What makes you think the other girl was gay? Your intuition might be telling you something.

January 11, 2015

Your sister 'despises homosexuality?' Generally young people are more blase and open. That could mean she is a lesbian if she's in denial. What makes you think the other girl was gay? Your intuition might be telling you something.

^My sister is one of those people that believes homosexuality isn't natural, plus one of our close relatives and gay, and she often clashes with this person cause of their sexuality.

As far as the other girl, my sister told me years ago that there were rumors in school that she was gay. She said she asked her, and she told it wasn't true. I don't know what's what, but I take people at their word and leave it at that.

She very well could be gay, but my initial gut tells me she isn't. If she is, then that's fine with me. As I mentioned earlier, I know the chances of me getting with her are slim to zero anyway. In time, this crush will pass over.

January 12, 2015

hit up your sister and have a serious conversation about how you want to date her friend, she should have an idea about if she may be into it, then if your only means of contact with this girl is facebook just start talking to her more, find out a mutual interest and try invite her out with you to it

January 13, 2015

hit up your sister and have a serious conversation about how you want to date her friend, she should have an idea about if she may be into it, then if your only means of contact with this girl is facebook just start talking to her more, find out a mutual interest and try invite her out with you to it

^I've already talked to my sister about it last year. Again, my sister encouraged me to hit her up through Facebook, however, I didn't do it because I didn't want to come across as an old guy hitting on young girls. I guess I care what she thinks.

I truly don't believe she is interested in me though. I've dropped little subtle hints, and I've done pretty much everything outside of telling her straight out that I'm interested in her, and she hasn't really responded in my opinion. Probably time to just let the crush go.

January 13, 2015

To be honest, when I was 23 I wouldn't have wanted to date a guy over 30. At that age I was still quite immature and 30 already seemed very old to me. You're just at different stages of life. I dated guys around 24-27 at that age. Now I'm 27 and I still wouldn't really want to date a guy who's ten years older than me. I'd say my max is around 33/34.

Anyway, not everyone thinks like me. I agree with the others here, talk to your sister first.

January 13, 2015

To be honest, when I was 23 I wouldn't have wanted to date a guy over 30. At that age I was still quite immature and 30 already seemed very old to me. You're just at different stages of life. I dated guys around 24-27 at that age. Now I'm 27 and I still wouldn't really want to date a guy who's ten years older than me. I'd say my max is around 33/34.

Anyway, not everyone thinks like me. I agree with the others here, talk to your sister first.

^Since I've already discussed with my sister how I feel, talking to her again is out of the question, mainly because I don't want to rehash it again. Judging from the responses that I've gotten here, the majority feel like it would be a bad idea to say anything to her, which is why I've yet to do so at this point. I view this as a strong indicator that I should probably just let it go, and let the flame die out eventually. Thanks for your feedback.

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Crushing on a woman younger than me. Should I tell her?

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