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I have a crush - how to flirt with him?


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Posted

So, I started volunteering recently and met this very cool guy. I've gotten a flirty vibe from him all along, and there's a palpable good energy between us. It seems we always gravitate to each other when we're working. Tonight, he asked some small talk questions at the end, like what I'm up to this weekend, etc. I noticed that lately we are both dressing up a little more for volunteering. I know I'm doing it to impress him! Not sure why he is, but I did notice it.

 

When I got home from volunteering today, my curiosity got the better of me and I Googled him. And I discovered that we have far more in common that I knew before. He's published and very active in one of my favorite creative fields and has a lot of online followers. All the things I already liked about him in person just took a few leaps up, now that I know what other cool things he's involved in. We share the passion for creativity and philanthropy.

 

So, my question is: how do I flirt with him? I already sense some flirty energy -- for example, he compliments me a lot, for even the smallest things (but volunteers are generally encouraging, kind people, so maybe he's just nice to everyone). And he's the director where I volunteer, so I'm thinking that might be a barrier to him being more direct. I want to make it clear I'm open to an approach, but not come on too strong.

Posted

If you're both into philanthropy, I'm guessing the volunteer work you do with him isn't the only volunteer work you do - or would be up for.

 

Maybe talk about some other volunteer work you do, or would like to do, and suggest that he join in... with a big smile on your face. ;)

Posted
"I just love helping people, don't you? Oops, dropped my pen, hold on let me slowly get that right in front of you."

 

+1.

 

Keep dropping him hints. He'll eventually catch on :p. Just make it unique and genuine because I sometimes feel like some people are just nice to me because they're nice to everyone.

 

By the way, what kind of volunteering is it? I am trying to meet new people but I am not really into the bar/club scene and would like to volunteer somewhere. Do you have any suggestions to get someone going?

Posted
So, I started volunteering recently and met this very cool guy. I've gotten a flirty vibe from him all along, and there's a palpable good energy between us. It seems we always gravitate to each other when we're working. Tonight, he asked some small talk questions at the end, like what I'm up to this weekend, etc. I noticed that lately we are both dressing up a little more for volunteering. I know I'm doing it to impress him! Not sure why he is, but I did notice it.

 

When I got home from volunteering today, my curiosity got the better of me and I Googled him. And I discovered that we have far more in common that I knew before. He's published and very active in one of my favorite creative fields and has a lot of online followers. All the things I already liked about him in person just took a few leaps up, now that I know what other cool things he's involved in. We share the passion for creativity and philanthropy.

 

So, my question is: how do I flirt with him? I already sense some flirty energy -- for example, he compliments me a lot, for even the smallest things (but volunteers are generally encouraging, kind people, so maybe he's just nice to everyone). And he's the director where I volunteer, so I'm thinking that might be a barrier to him being more direct. I want to make it clear I'm open to an approach, but not come on too strong.

 

Ruby,

 

Glad to see that you are back in the game. I do find it a little hard to believe that you don't know how to flirt:laugh:.

 

I would say thought that find a mutual interest outside of volunteering. That way you can invite him to an activity outside of volunteering where he maybe able to lower his guard.

 

I know that would work for me.

 

Also, I don't know if it is your style, but physical touching will let him know you are interested.

Posted

I say just try to let your interest be known through body language and through subtle hints like complimenting him back. Above all though, smile! :)

Posted

You know what drives me wild? When I catch a woman checking me out (in the work place or some other kind of professional setting) and when she knows I'm on to her she sorta rolls her eyes and looks away slyly like she's admitting that she's busted. Then I like seeing a sort of proud strut as she walks away. If I think she's good looking and interesting, that little scenario makes me feel like a million bucks, but it's not just ego because it starts to get under my skin that SHE makes me feel like a million bucks. Then I start thinking, geez, what about me and her? I don't know if that reads very well or makes any sense but I've had it happen in professional situations where it's inappropriate to trot over there and flirt out-right. It makes such an impression though that it can create a magnetic pull. It's not something you want to wear out but it's sexy as hell. Then if he looks like he's desperate for an "in" to find out if there's something, you put your hand into your blouse near your heart and pump it a few times and telegraph that he makes your heart thump. Sorry, I'm just ad libbing. But it would totally work on me.

Posted

Hey Ruby,

 

Getting him to ask you out is an excellent method to start flirting. He might feel uncomfortable if the two of you did it at the workplace (I wouldn't!), so a little date might be a great place to start. Maintaining eye contact, remembering what he said or likes and starting new conversations based on what he said are great ways to get him lower his guard.

 

Once that happens, he'll be susceptible to some good old flirting tactics. Turning your head slightly from time to time to show nice angles of your face, exposing your neck, showing the inner parts of your wrist and maintaining strong eye contact are slight turn-ons.

 

To really turn him on, find excuses to touch him. Like by putting your hand on his lap as you recall a past experience and laugh. Or catch his attention when (if) his mind seems to be drifting by rubbing your foot against his leg.

 

Stuff like that really turn guys on. I'm sure you have a few more tricks up your sleeve that'd work on him, so do all you can do, but be sure you don't seem to desperate while at it.

 

Max

Posted

The fact that he asked you what you were doing over the week-end is an excellent sign that he could be interested. Is he on the quiet side? Possibly he was hoping that you would ask him out. You could ask him if there are any holiday get togethers/parties coming up where you volunteer. If he is the quiet type it may be up to you to suggest something.

Posted

Shouldn't this be moved to the "Flirting" subforum?

  • Author
Posted (edited)
The fact that he asked you what you were doing over the week-end is an excellent sign that he could be interested. Is he on the quiet side? Possibly he was hoping that you would ask him out. You could ask him if there are any holiday get togethers/parties coming up where you volunteer. If he is the quiet type it may be up to you to suggest something.

Oh, good. :D Yeah, when I told him my plans, he said that sounded really good. But it's a get-together with close friends, so I couldn't really invite him along. If I had been going to some event, I might have opened it up to him. And then I asked what he was doing, asked follow-up questions, kept it going.

 

There are holiday parties coming up, and I had to miss the Halloween one. But I am not missing the Thanksgiving one -- in fact, I'm going to cook or bake something really good for it. :D

 

Yes, he does seem to be a little on the quiet/shy side. At the same time, he's obviously a leader in several ways. We have this totally in common. I LOVE the way he is with the kids, and the other volunteers. A lot of these kids don't have father figures at all, and it always hits me how good it must be for them to have him around. He's patient, fun, cool, smart, and he has a way of saying big, profound things to them on a level they can understand.

 

I notice that whenever we do group activities with the kids, he ALWAYS sits next to me. And yesterday, he was taking pictures of the groups with his phone, and he seemed to be making me the focal point of all of them. And yes, I was putting on my best smile. :D

 

In the past, more than one guy has told me I don't give off strong signals of interest, even going so far as to say they had no idea I was interested, I wanted them to kiss me, I wanted them to make a move, etc. I think what happens is that I'm burning up inside but trying to play it cool on the outside. Well, with him, I'm trying to let the fire out a bit.

 

By the way, what kind of volunteering is it? I am trying to meet new people but I am not really into the bar/club scene and would like to volunteer somewhere. Do you have any suggestions to get someone going?

We tutor and mentor the most disadvantaged kids. (And he and I have this in common, too -- we both grew up poor, overcame it, and want to help people who are in the position we were.) I don't want to get into too many specifics, as now I'm paranoid about him finding this thread somehow (ha). Some cities have databases you can use to search volunteer opportunities. I found a good one in my city and started there, searching on education, tutoring, mentoring. You can volunteer in just about any area you can think of, and it is a great way to meet awesome people. Go for it!

 

Thanks for all the flirting ideas. I am NOT comfortable asking him out. I have never in my life asked a man out. And if he didn't want to go, it would be awkward afterward. I think if anyone does that, it's going to have to be him.

 

But I will keep making conversation, and I'm going to start telling him how great I think he is at what he does. And as soon as I have the opportunity to escalate to touching him without it being weird, I will. He has such sexy hands. I totally want to touch him. :love:

 

Shouldn't this be moved to the "Flirting" subforum?

No way. I'm hoping that soon we'll be dating. :love:

Edited by Ruby Slippers
Posted

God.

 

There's so many ways.

 

Two of the most effective as far as I'm concerned are 1) smiling and batting your eyebrows and 2) wearing a V neck shirt that exposes your cleavage slightly but not enough to be slutty with a necklace that rests ever so coyly between them. :o

 

Hey, honest answers.

 

Also, if he's anything like me, he'll have mistaken womens' friendliness for flirting in the past and maybe never act on it.

 

Why not just ask him out? If he's not a real good looking guy, he's probably not used to that and it will be flattering.

Posted

Thanks for all the flirting ideas. I am NOT comfortable asking him out. I have never in my life asked a man out. And if he didn't want to go, it would be awkward afterward. I think if anyone does that, it's going to have to be him.

 

It never ceases to amaze me how women could be so picky about what they want in a man, and when that man finally comes along, they don't have the cojones to simply ask him out.

 

Man. Bite the bullet and go for it.

Posted

 

But I will keep making conversation, and I'm going to start telling him how great I think he is at what he does. And as soon as I have the opportunity to escalate to touching him without it being weird, I will. He has such sexy hands. I totally want to touch him. :love:

 

 

No way. I'm hoping that soon we'll be dating. :love:

 

Be really careful. This has all the makings of a serious puppy crush. Googling the guy?

 

I'd just ask him out ASAP before you get yourself too invested and gaga into the whole thing.

 

Trust me...

Posted
So, I started volunteering recently and met this very cool guy. I've gotten a flirty vibe from him all along, and there's a palpable good energy between us. It seems we always gravitate to each other when we're working. Tonight, he asked some small talk questions at the end, like what I'm up to this weekend, etc. I noticed that lately we are both dressing up a little more for volunteering. I know I'm doing it to impress him! Not sure why he is, but I did notice it.

 

When I got home from volunteering today, my curiosity got the better of me and I Googled him. And I discovered that we have far more in common that I knew before. He's published and very active in one of my favorite creative fields and has a lot of online followers. All the things I already liked about him in person just took a few leaps up, now that I know what other cool things he's involved in. We share the passion for creativity and philanthropy.

 

So, my question is: how do I flirt with him? I already sense some flirty energy -- for example, he compliments me a lot, for even the smallest things (but volunteers are generally encouraging, kind people, so maybe he's just nice to everyone). And he's the director where I volunteer, so I'm thinking that might be a barrier to him being more direct. I want to make it clear I'm open to an approach, but not come on too strong.

 

Ruby:

 

You are not a 16 year old kid anymore. If you don't know how to flirt by now you might as well call it quits.

 

However, I will admit that flirting can be a natural talent that is hard to acquire, but at your age I would think you have a clue.

 

Look at him and then cast your eyes away in subtle coy manner. Always touch him while talking to him. Dress with a skirt; men respond quite well to legs. Play dumb so he can help you out, that is usually a winner.

Posted
You know what drives me wild? When I catch a woman checking me out (in the work place or some other kind of professional setting) and when she knows I'm on to her she sorta rolls her eyes and looks away slyly like she's admitting that she's busted. Then I like seeing a sort of proud strut as she walks away.

Ha, ha. that is the reaffirmation game women play.

 

Some men act to intense with the signals and that turns the women off. The mating game is suppose to be subtle with a to and fro component.

Posted

She could ask him out to get lunch. Women ask me to go to lunch all the time in a work setting and it is an acceptable move that is not too intense. It is important to be subtle.

 

Asking the date out on a formal romantic date is not a good idea.

  • Author
Posted
It never ceases to amaze me how women could be so picky about what they want in a man, and when that man finally comes along, they don't have the cojones to simply ask him out.

 

Man. Bite the bullet and go for it.

This guy is my supervisor. If this were paid employment, he'd be my boss. So it would be awkward if I asked him out and he said no.

 

Be really careful. This has all the makings of a serious puppy crush. Googling the guy?

 

I'd just ask him out ASAP before you get yourself too invested and gaga into the whole thing.

Oh, it's too late for that. I already have a puppy crush. But I'm loving the energy. I hardly know him at this point. For all I know, he has a girlfriend or is married. If he reveals this to me, it's going to take an iron will to hide my disappointment.

 

If you don't know how to flirt by now you might as well call it quits.

:rolleyes: This is a unique situation. He's not just some guy. He's my supervisor in a professional environment. So it's a little trickier.

 

Dress with a skirt; men respond quite well to legs.

I have worn a form-fitting sweater and cute fall skirt and boots the past 2 weeks, with tights, and I have seen him checking out my legs both times. (I have a great set of getaway sticks.) :D

 

Play dumb so he can help you out, that is usually a winner.

I have started doing this a little, too. Not playing dumb, but letting him take the reins more. The first week or 2, I was more assertive and making things happen. Now, I hang back a little and let him do it when possible.

 

There was a very cute moment the other day. I'm tall, so shorter people always ask me to get things from the top shelf for them. He's maybe an inch shorter than I am (and I don't care). The other day, he reached up to a top shelf to pull something down for me, handed it to me, and said, "Thank you for letting me get that for you." I just got this huge grin on my face, said, "You're welcome. And thank YOU." :love: :love: :love:

Posted
This guy is my supervisor. If this were paid employment, he'd be my boss. So it would be awkward if I asked him out and he said no.

 

 

There was a very cute moment the other day. I'm tall, so shorter people always ask me to get things from the top shelf for them. He's maybe an inch shorter than I am (and I don't care). The other day, he reached up to a top shelf to pull something down for me, handed it to me, and said, "Thank you for letting me get that for you." I just got this huge grin on my face, said, "You're welcome. And thank YOU." :love: :love: :love:

 

If you start dating, how is that going to be any better? If it's a volunteer situation, it's NOT the same as a full time employed job. If you lose your non-paying job, so what.

 

Awww. That's cute. I wish I was less bitter over being rejected in these types of situations. I could give you more optimistic advice. I hope you guys hook up. I really do. Good luck. :)

Posted

There was a very cute moment the other day. I'm tall, so shorter people always ask me to get things from the top shelf for them. He's maybe an inch shorter than I am (and I don't care). The other day, he reached up to a top shelf to pull something down for me, handed it to me, and said, "Thank you for letting me get that for you." I just got this huge grin on my face, said, "You're welcome. And thank YOU." :love: :love: :love:

He definitely likes you. :) The only thing that can get in your way is a partner, but so far, it does look good. :)

  • Author
Posted
He definitely likes you. :)

:bunny: :bunny: :bunny::love: :love: :love:

 

The only thing that can get in your way is a partner, but so far, it does look good. :)

I know. He has thousands of FB friends, and there's lots of pictures of him at his performances and events where cute women are smiling at him adoringly. :mad: Back off, bitches!!! :p

Posted

Is he shorter than you when you have flat shoes?

 

If you have good legs I was going to suggest high heel pumps. They not only enhance the legs, but create a very sexy look for the whole female figure with accentuation of the chest and gluteal area. You can try them with a business suit and does not look slutty.

 

If you have pointy boobs you may want to accidentally push your boobs into his side or back when you walk by. That is always a very positive signal.

 

Fake a neck spasm to see if he offers to rub your neck. If he does try to look horny.

 

Make sure you are touching and grooming your hair when you are talking to him, that is a universal sign of female flirtation.

 

Act a bit demure and coy when he glances at you. You need to project the sensation you are melting when he does that.

 

The above comes naturally for some women and not for others. Not sure why.

  • Author
Posted
Is he shorter than you when you have flat shoes?

I think we are about the same height flat-footed. The boots I have worn lately have a bit of a heel.

 

If you have good legs I was going to suggest high heel pumps.

I am not wearing high heels to tutor low-income kids when everyone else is wearing casual clothes. It's already a notch up that I'm wearing skirts, boots, etc. Heels would be way overkill.

 

If you have pointy boobs you may want to accidentally push your boobs into his side or back when you walk by. That is always a very positive signal.

I am not pushing my boobs into him! First, he's my supervisor. Second, there are kids everywhere.

 

Make sure you are touching and grooming your hair when you are talking to him, that is a universal sign of female flirtation.

Yes, you're right about this. I already do this whenever he talks to me, almost involuntarily.

 

Act a bit demure and coy when he glances at you. You need to project the sensation you are melting when he does that.

Yep, I do that, too. Can't help it.

 

Man, I can't wait till volunteering next week. :bunny:

Posted (edited)

Ruby,

 

It all sounds good. (One never knows, of course, but from your description, I'd say it's only a matter of either time/patience or giving him an obvious in---take your pick as to which you'd rather.)

 

If it were me, I'd just go out and ask if he was interested in getting together outside the volunteer site. But I'm the go-for-it type. I usually do that when I know the guy is likely going to ask me out. . . someday. But I'm getting sick of waiting. Which is what this sounds like to me.

 

All you really need to do is keep doing what you're doing, be social, be available, and then drop him a few hints (great ideas in this thread) when appropriate. And I'd wager he'll ask you out by Christmas anyway.

 

ETA: Hey, he's a director for tutoring low income kids? That's funny --- that's part of what I do. But bad news. . . I'd never go out with any of our volunteers (and certainly not the hired tutors). In this field, there's sometimes not a lot of wiggle room, assuming he's a salaried employee. It's basically forbidden in my contract. Not sure who he works for, but my foundation would fire me immediately. :(

Edited by zengirl
Posted

 

If you have pointy boobs you may want to accidentally push your boobs into his side or back when you walk by. That is always a very positive signal.

 

Pierre! I'm kind of shocked at this suggestion from you. Boob poking is kind of … aggressive, don't you think?

 

Fake a neck spasm to see if he offers to rub your neck. If he does try to look horny.

 

Is he rubbing her neck from the front, so he can observe the horny face? This might seem more like strangulation ...

 

 

Act a bit demure and coy when he glances at you. You need to project the sensation you are melting when he does that.

 

Now, that's more like the kind of tips we should be able to count on from an old-school gentlemanly type such as yourself!

 

:p

Posted

Many men love women with a nice, tall pair of legs:love:

 

So strut them bad boys and go get 'em Ruby:love: Remember, fate favors the bold:cool:

 

 

Another :love::love: for RS, because she's one of my favorite LS women.:love:

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