How to let a younger guy know I'm interested?

[Anonymous]

Here is my dilemma: there is a younger guy at work I'm starting to notice. A few times we talked I got the vibe he might be interested. I don't initiate any conversations but the few we had he did and we both enjoyed it.
I got the vibe that he tries to impress me but at the same time he quite self-deprecating which I like because I'm the same way.
Since it's work I would have to really subtle because you never know. On top of that, I don't even know if he's seeing anyone.
What should I do to make sure he knows I'm interested?
I'm 42 and he's 35.
If you're going to post that I'm too old for him and all that, spare yourself some time and energy and just don't say anything.

[abc3643]

This is normal male behavior. Because you are older, but both of you are not old, he will still retain a certain boy-instinct of being deferential to older females. After all, when we are very young, we are surrounded by older and larger females who have great power in our lives so that power older females have over us does not really diminish until we reach our 40s at least. So, yes, he can be interested and may express it a bit, but, at a subconscious level, he will still be a little boy a bit and fear disappointment of not being approved by an older female. So, take the lead. The way to do this is, whenever he does anything positive toward you, be vocal in expressing thanks and gratitude and approval. This is all positive reinforcement. With that, he drops his guard a bit and instinctively and subconsciously his fear of disapproval from the older female begins to dissipate. At some point, you can take the lead by inviting him to go with you to something harmless like some public social event. That is a "non-date" date among friends, but a few of those quickly becomes de facto dating and leads to a relationship.

Stay positive. You are in control and will reel him without much difficultly as long as you don't scare him off with negativity.

[Asker]

Great comment! Very informative and I tend to agree with everything you said. I have noticed that whenever we talk he looks for my approval and almost a permission. He will say things like: so you want me to? Or " Would you like me to.."?
What you think about that?
Is he expressing interest or showing an intimidation?

[abc3643]

Not intimidation but respect.

Let me give you an example...
In 1996, I was 33 years old and still a good-looking guy who had good hair - the kind women liked. Back then, I still smoked. At my desk, sometimes this beautiful woman would come walking by rather fast to go to some VIPs office. I never got a good look at her face. However, after awhile, when I went outside to smoke, I would see her. We became friendly. Now, I was heartbroken back then, but rather secure in my masculinity and felt I could get a woman my age if I wanted. Anyway, once I met her outside, it was obvious this woman was older than me by at least a decade. Still, she was beautiful and __hot__. I would later learn she was 15.5 years older than me. That would not have been a problem for me. We became good friends and I'd be at her house quite a bit. She was smart and obviously more experienced than me so she sensed I would have been happy to be her man, but she was a free spirit and never encouraged me. (more)

[abc3643]

But, back for a minute... I was secure in my masculinity and ease in communicating with any woman in my age group or younger, but not her. She was only 4 years younger than my mother and she was still rather beautiful that I had this combined awe and respect of her - awe from her attractiveness on so many levels and respect because she was older - she knew more, had more experience (and, while I was 33, I was not that experienced). I deferred to her; she always had the power, control, and lead in our friendship and non-romance.

[abc3643]

And I do think he is interested.

[Asker]

Oh man! I know you're trying to say. For some reason I get more interest from younger guys than men my own age. I don't complain, I love it but... I feel like with most of them is a combination of intimidation and infatuation that eventually leads nowhere. I like younger guys because I like men who are confident yet still have that air of innocence. It's very appealing to me. This guy, in comparison with his peers seems more confident which I like a lot.
If you're saying he's interested, I go with that. What else would he do if he were?

[abc3643]

He is a dog. He is loyal and loving as long as he is paid attention to him.

by the way, something else: For many of us - definitely me - we have a thing for older women. Implicitly, we value older females over those of our age or younger because we were raised that way. When you are a 5 year old boy, who is beautiful and who's wrath do you fear and who's love do you seek? The older giant females around you. They are the real rulers in your world, not the men. You may fear the men or older boys when you are a young boy, but you don't seek their love really. You see the love of those older women. So, for the first 2 decades of life at least, the older female is the target of our fantasies and her approval and choosing us is the ultimate in approval that we seek. When we are boys, we respect those elder women, but not the other girls our age. Those girls don't have power over us, like the older women do.

Even today, my wife is 5.5 years older than me.

[Asker]

I see where this is coming from. It's a good theory and it makes a lot of sense.
My mom is older than my dad too.

[abc3643]

There you go. You should ask your dad about it... or your mom...

[Asker]

They both say I need to settle down with someone my own age LOL

[abc3643]

35 is close enough to 42. That's a trivial age difference at that point. I was 36 when I met my wife who was 42.

[Logorithim]

You're definitely not too old for him. Suggest that you eat lunch together so you can talk to him some more and get a better idea of whether he is someone you might want to date or is even available. You can always camouflage it as a "working lunch".
The best subtle sign to a guy that a woman is initialy interested in him is when she initiates friendly conversations with him and spends some time with him.

[ArtsyAlly]

I'm dealing with the same situation, except that it's a friend of mine, not a coworker, and I'm 30 and he's 23. I know it's been hard for me to ask him out or anything like that because I don't want to lose his friendship or make things awkward. Do you feel like things would get extremely awkward if you were to ask him out and he said no?

[Asker]

It might just feel awkward for a minute. Then I would just move on like nothing happened.
I think it's easier with a friend because you already know him. I know close to nothing about this guy, even though he shares some personal stuff everytime we talk.
Do you think your friend is attracted to you?

[ArtsyAlly]

I wish I knew! LOL! There are signs here and there that could point to it, but I honestly don't know for sure. I need to be hit in the head with an anvil to know if he likes me or not haha.

[thomascale18]

You could just ask him out to lunch. Also, are you trying to make this a long term thing or a one night stand? If the latter, then the older age would work in your favour. If the former, then you obviously need to take your time and slowly help him grasp the idea that age doesn't matter.

[Asker]

I don't like older guys LOL
Lunch won't do because his team has always lunch together or they just work through lunch :(
I just want to get to know him a bit and see where to take it from there.

[thomascale18]

I meant your older age. How about a movie then? Basically just ask him out somewhere.

[Asker]

Got it. I don't know if I want to date him. I was just thinking of having fun if you know what I mean.

[thomascale18]

Then go for it. It would be such a huge turn on for me if an older lady asked me out and we had some fun.

[GingerGuy]

Yes you have to be cautious being a work environment however you'll have to make the first move as well (guys risk sexual harassment etc). Start initiating some conversations and flat out ask him if he's married or seeing anyone. To make it less obvious, you could just say "do you have any kids, wife, girlfriend?" This is a common question guys get asked by co-workers. Then, (either then or another time) casually ask him if he'd like to grab a coffee with you (or dinner) outside of work.

[Wytdrgn]

There's one thing you could do that will answer all your questions. Tell him your throwing a little get together and it would be nice if he came to it. If he accepts ask if he will be bringing anyone with him. This way you find out if he is single or not.
A little casual party is a good way to get to know each other better and find out his real feelings.

[thechico79]

too old? no way I date a 45 year old. when I was 35.
Do you have his #? if so just send him a text stating that it has been some time building but I have an interest in you, and I was wondering if you are taken? If not what would you think if we can go for lunch/dinner one day?

[Brewmaster531]

If he's not seeing anyone, there isn't an issue. Don't do too much different than you would for someone your age. He won't be freaked out by it. Go ahead and just let him know. He'll be absolutely intrigued.

[WalterRadio]

If you are the older one, just come right out and lead, "You know, I think you are cute. Would you like to come to my house on Friday night? I'll make you dinner."

Trust me, he will come and bring a condom.

[ITKing]

Nothing good will come from dealing with a coworker on that level. Trust me... done it plenty of times. Save yourself the trouble and find someone you don't work with.

[talk2dream]

try just telling him you'd be interested in a discrete coffee outside work... but want to keep work life normal?

[Asker]

That could work but the truth is I'm hoping he'll initiate something first.

[Fusion83]

Why not reciprocate more
Dont let him be the only one to start conversations
Maybe ask him a hypothetical about a younger guy dating an older woman he works with and see what he says

[Iamaguy4real]

You can try to get his attention by looking at him, playing with your hair, vet nervous around him, etc

[AlwaysBelieving]

Since it's at work, do you have any mutual work mates that you could "inquire about him"?

[SuccessfulHornDog]

Tell him that you need a spanking or a thorough fingering. He'll understand

[Humbledman74006]

Ask him for coffee outside work... maybe a day at. the zoo, see where it goes

[vic_tor]

Being older, just be straightforward and tell him what you have in mind..
That would definitely please me if i was in his place

[armedtoteeth]

A week of your hottest outfits.. and who are you kidding I love older women

[Anonymous]

Kick his balls. Young guys like their balls kicked.

[GlennGc]

I dont think its wise to date coworkers :/

[TheChatWanderer]

True

[mikeybk]

And no way you're too old for him

[mikeybk]

There's no way I like women my age and I don't give a shit if it makes me look superficial it's just the truth so I suggest if you like him be bold and go up and just tell him

[mikeybk]

The worst he can say is no

[itriedabunch]

Go for it. probably be good for u

[I602I]

that isn't even a big age gap in my opinion

[Anonymous]

just tell him