How does one "flirt" without being awkward?

[Inflikted]

Let me give some context first. Actually, let me give some "context" to the context before that. I'm a 28, nearing 29, year old guy that's always been extremely socially awkward and inept, never dated, never even been in anything resembling a flirtatious conversation with a girl.

 

So, the other day at work (I work in a retail/ customer service job), after finishing up helping a customer, my two female coworkers were kind of teasing me about me apparently being totally oblivious to the fact that the girl I was helping was flirting with me.

 

Granted, I'm not sure how accurate their intuition was, because I'm not exactly a charming, likable, or physically attractive guy, and the girl, in question, was so far out of my league that a guy like me shouldn't even be on her radar. But I also can't help but wonder... what if?

 

Although, in this case, I'm sure I've already blown any chance I had by being my awkward and oblivious self (if I even had a chance at all to begin with, that is), and even if she comes in again, there won't be any "second chances", but it really put into perspective for me how woefully unprepared I am for potential "flirting"/ dating.

 

I mean, half the time, I can barely hold a conversation in a platonic scenario. I can't even wrap my head around "flirting" or pursuing something more than friendly with someone.

 

I also don't know how to handle that type of thing while I'm at work. Like... it feels extra awkward trying to "flirt" with a customer, because if I read things wrong or if I'm just my awkward self, I don't want to come off bad professionally. I dunno.

[CptInsano]

Let me give some context first. Actually, let me give some "context" to the context before that. I'm a 28, nearing 29, year old guy that's always been extremely socially awkward and inept, never dated, never even been in anything resembling a flirtatious conversation with a girl.

 

So, the other day at work (I work in a retail/ customer service job), after finishing up helping a customer, my two female coworkers were kind of teasing me about me apparently being totally oblivious to the fact that the girl I was helping was flirting with me.

 

They were probably right. Women pick up signals from other women earlier than most men do.

 

Granted, I'm not sure how accurate their intuition was, because I'm not exactly a charming, likable, or physically attractive guy, and the girl, in question, was so far out of my league that a guy like me shouldn't even be on her radar. But I also can't help but wonder... what if?

 

Why do you think that? Just because you're socially awkward? Seriously, you never know who may be interested in you. I've had women flirt with me from African American to Inuit, through all levels of attractiveness. You cannot tell from the looks of the woman if she is interested in you or not.

 

Although, in this case, I'm sure I've already blown any chance I had by being my awkward and oblivious self (if I even had a chance at all to begin with, that is), and even if she comes in again, there won't be any "second chances", but it really put into perspective for me how woefully unprepared I am for potential "flirting"/ dating.

 

I mean, half the time, I can barely hold a conversation in a platonic scenario. I can't even wrap my head around "flirting" or pursuing something more than friendly with someone.

 

Yes, learning how to hold a simple conversation with friends would be a start. A flirt has a slightly different dynamic, but you won't be able to get far without small talk.

 

I also don't know how to handle that type of thing while I'm at work. Like... it feels extra awkward trying to "flirt" with a customer, because if I read things wrong or if I'm just my awkward self, I don't want to come off bad professionally. I dunno.

 

Just let her take the lead if you are unsure, reciprocate but don't escalate, and you will be largely on the safe side.

[Inflikted]

Why do you think that? Just because you're socially awkward? Seriously, you never know who may be interested in you. I've had women flirt with me from African American to Inuit, through all levels of attractiveness. You cannot tell from the looks of the woman if she is interested in you or not.

 

Well, more so because by the typical male standard, she was a very attractive woman, and in comparison, I'm a short, pudgy, pasty, baby-faced dope. Like, to me, it just doesn't quite add up that someone who could date someone WAY more attractive than me would be interested in me in that way at all.

 

Yes, learning how to hold a simple conversation with friends would be a start. A flirt has a slightly different dynamic, but you won't be able to get far without small talk.

 

I find that, in general, I tend to "loosen up" a little more with people after I've had a number of interactions with them. I'm awful at first impressions, and usually second and third impressions, as well. Even when all do open up more, all I really have to offer is the occasional chuckle-worthy one-liner. I don't care much for small talk, but I'm not "socially intelligent" enough to know how to start and have good conversations.

 

I've always been a bit backwards that way. I was raised in by two very unsociable parents, and I never felt like I'm properly equipped to break that trend. When it comes to social situations, be it platonic or "flirtatious", my mind is typically blank. Like, I legit just never know what to say.

[alphamale]

You cannot tell from the looks of the woman if she is interested in you or not.

 

that's the truth

[preraph]

Some women are just naturally outgoing and flirty -- and some of those women have a wide range of men they find attractive, but there is never any way to know for sure. You just have to be friendly back. If she was focused on you, she'll be back.

[carhill]

OP, since this has been a long-term issue, IMO it's beyond self-help or forum advice and more in the realm of professional help.

 

Today, on descent, I complemented our FA on her exemplary service then added 'bonus points for the red heels' with a wink. She could've taken that a number of ways but our banter prior clearly indicated to her what my intent was. It was a moment, hopefully a bit of fun in an otherwise often tedious workday for a flight attendant, and it was all true from my perspective. She treated her first class passengers amazingly well and really did look hot in her red heels.

 

No expectations, just having some fun. People do what they do, life goes on.

[Shanex]

You cannot tell from a woman's look if she's interested or not.

 

That was a true statement. On the other hand, it's pretty easy to know if she isn't. Though I cannot lump all women together I find them more forward in letting you know whether they like you or not, maybe less hypocritical than men. Unless of course she is a total manipulative beast. Usually I can tell if a woman is not interested in which case I politely move away.

 

If that girl was flirting with you which is true here imo. She will be back at your store for sure.

[LivingWaterPlease]

OP, you're getting some great advice on this thread! What carhill said, "Just have some fun!" to me sums up flirting perfectly!

 

Also, others have advised that you can't tell by the level of her attractiveness whether or not a woman would be interested in you or not and I agree.

 

For one thing, some people have an eye for beauty/good looks and some don't.

 

If you keep yourself clean, smelling good, well groomed, forget about impressing the ladies, and just learn how to have fun joking around casually with them with no goal of getting into a relationship with them, you'll find a lot of ladies will want to be in your company!

 

Frankly, you may be as you described, not a looker, but I find your posts very appealing. You are the type of guy I would enjoy spending time with and having fun with because you seem warm, authentic, and also intelligent! I'm way too old for you (and I prefer old guys like me, lol!) but if I were your age I'd be interested in you (or if you were an old guy I would, too!) Just saying!

 

i think you're going to be just fine with a little practice in being light hearted. And FWIW, lots of other guys are clueless about whether or not a lady is interested in them, too.

 

PS I do think you're wise to be cautious about getting too flirty on the job, though. You want to keep things professional so you don't put your job in jeopardy!

Edited May 13, 2017 by LivingWaterPlease

[Inflikted]

Today, on descent, I complemented our FA on her exemplary service then added 'bonus points for the red heels' with a wink. She could've taken that a number of ways but our banter prior clearly indicated to her what my intent was. It was a moment, hopefully a bit of fun in an otherwise often tedious workday for a flight attendant, and it was all true from my perspective. She treated her first class passengers amazingly well and really did look hot in her red heels.

 

No expectations, just having some fun. People do what they do, life goes on.

 

Heh, I wish I had that type of confidence to have that sort of charm or charisma.

 

You cannot tell from a woman's look if she's interested or not.

 

Sure, but I mean, physical attraction tends to be some level of a factor for people, and I can't really wrap my head around why someone "attractive" would be attracted to me. That just... doesn't really add up to me.

 

On the other hand, it's pretty easy to know if she isn't. Though I cannot lump all women together I find them more forward in letting you know whether they like you or not, maybe less hypocritical than men. Unless of course she is a total manipulative beast. Usually I can tell if a woman is not interested in which case I politely move away.

 

Yeah, I dunno, in the past, there were times I thought a girl may have been interested in me that way, but I was wrong, and the awkwardness resulted in that person pulling away. So, generally speaking, I tend to operate and live my life under the assumption that no one is "attracted" to me or interested in me for anything other than something platonic, and that any "special attention" I get from anyone is just them being nice or more social than normal.

[Inflikted]

OP, you're getting some great advice on this thread! What carhill said, "Just have some fun!" to me sums up flirting perfectly!

 

I can see how that makes sense, yeah. Me, personally, I have a hard time understanding what's "fun", and I'm also very nervous about crossing lines with people. Like, because I know my penchant for being awkward, I'm more likely to be very quiet and reserved around someone I haven't known for very long, because I'd rather do that than to say something that inadvertently crosses a line or makes the other person uncomfortable, or anything like that.

 

Unfortunately, more often than not, in my experience, I don't know that I'm "crossing a line" until it's too late. Hence why I tend to be reserved and detached, because I'd rather than to create an unpleasant scenario for someone else.

[LivingWaterPlease]

I can see how that makes sense, yeah. Me, personally, I have a hard time understanding what's "fun", and I'm also very nervous about crossing lines with people. Like, because I know my penchant for being awkward, I'm more likely to be very quiet and reserved around someone I haven't known for very long, because I'd rather do that than to say something that inadvertently crosses a line or makes the other person uncomfortable, or anything like that.

 

Unfortunately, more often than not, in my experience, I don't know that I'm "crossing a line" until it's too late. Hence why I tend to be reserved and detached, because I'd rather than to create an unpleasant scenario for someone else.

 

 

Takes practice, Inflikted! Practice forgetting about yourself and what others will think of you. Focus on the good about others and take the risk of putting yourself out there to make them feel good about themselves, not to be funny in order to entertain. Notice carhill complimented the FA on her red high heels! Include a compliment in your fun comments.

 

Most people feel awkward at times and many have to learn how to enjoy others. Practice is key! you can do it!

[bebe23]

Well, more so because by the typical male standard, she was a very attractive woman, and in comparison, I'm a short, pudgy, pasty, baby-faced dope.

 

You are? "Short, pudgy, and baby faced" perfectly describes my biggest Hollywood celebrity crush right now, Josh Gad. He's cute to me BECAUSE of that, not in spite of it.

It just goes to show that there is something appealing about everyone to someone. It sounds like you (just like that other poster ZA Dater) need to work on your self esteem and social anxiety through counseling.

[Titanll]

You can change pudgy and pasty. Sorry on the height thing. Getting in better physical shape may give you a little more confidence. Enlist the girls at work to give you advice on how they flirt. Hell, ask them to show you some sex tips haha! May be fun.

[Inflikted]

Takes practice, Inflikted! Practice forgetting about yourself and what others will think of you. Focus on the good about others and take the risk of putting yourself out there to make them feel good about themselves, not to be funny in order to entertain. Notice carhill complimented the FA on her red high heels! Include a compliment in your fun comments.

 

Most people feel awkward at times and many have to learn how to enjoy others. Practice is key! you can do it!

 

I mean, I feel like I've been trying to "practice" for several years, now, and I don't really feel I've gotten any better at it, nor do I feel like I really understand it any better than I did, like, ten years ago. I've met and known tons of people over my life, and I've had plenty of opportunity to "practice" and learn how to be a normal, social person, and how to have normal interactions with people, and how to have normal romantic pursuits, but none of it "clicks" with me. I've tried, and I've tried, and I've tried, but I'm still basically as awkward and socially inept as I've always been.

 

You are? "Short, pudgy, and baby faced" perfectly describes my biggest Hollywood celebrity crush right now, Josh Gad. He's cute to me BECAUSE of that, not in spite of it.

It just goes to show that there is something appealing about everyone to someone. It sounds like you (just like that other poster ZA Dater) need to work on your self esteem and social anxiety through counseling.

 

You can change pudgy and pasty. Sorry on the height thing. Getting in better physical shape may give you a little more confidence. Enlist the girls at work to give you advice on how they flirt. Hell, ask them to show you some sex tips haha! May be fun.

 

Truth be told, despite how I describe myself, I'm pretty much at peace with who I am. Even if I lost a few pounds and toned up, I'd still be awkward and inept, not to mention, I don't think I'd have much of a drive to maintain that appearance.

 

I'm okay with what I look like, but I'm also self-aware to know my flaws and to understand where I fit in on the scale of attraction. So, again, I just can't wrap my head around the idea of someone way higher up on the scale possibly being attracted to me.

[CptInsano]

Truth be told, despite how I describe myself, I'm pretty much at peace with who I am. Even if I lost a few pounds and toned up, I'd still be awkward and inept, not to mention, I don't think I'd have much of a drive to maintain that appearance.[...]

 

Think of it as something that you'd do for yourself and not for others. You may just be surprised how good it feels. Don't think of it as a chore, but rather an investment in yourself.

 

I'm okay with what I look like, but I'm also self-aware to know my flaws and to understand where I fit in on the scale of attraction. So, again, I just can't wrap my head around the idea of someone way higher up on the scale possibly being attracted to me.

 

Then take your head out of the game. I was an awkward teenager at 17, and I remember a girl at a party asking me three times (bless her heart) to leave the party and go stargazing with her. I responded that the light pollution was pretty bad in this part of town. I was so wrapped up in what I thought I should do, and who I should ask out, that I completely overlooked the obvious.

[Gillys]

You’re in luck my friend, you ‘re in the perfect industry to practice flirting.

 

To me, flirting is all about being authentic, warm and making the other person feel comfortable. Making a girl laugh is always a plus! If you’re able to throw in some natural witty banter you’ll be golden (again this take practice to not come off as fake).

 

How to not cross the line and remain professional: Absolutely zero sexual innuendo and inappropriate touching. Basically, anything that can get you fired from work aka be respectful.

 

How to know if a girl is flirting with you or at least welcoming your company: Try to pick up on body language (is she making eye contact, facing you squarely, finding little ways to touch you, laughing at your jokes even if they aren’t funny, awkwardly lingering hugs or touches) not saying all of these are signs she wants you, but good signs that a woman isn’t bothered by your company.

 

As far as looks: everyone finds different things attractive. As a female, I think personality is more attractive than the physical sometimes. Not to toot my own horn but 10 years ago while I was in undergrad, I got approached much more (by men and women) than my more attractive female friends because of personality. There is something to be said about personality and having the confidence to carry on a conversations and make someone feel comfortable.

 

I think one of your problems may be mindset. No one is out of your league based on looks. I’ve had some physically attractive friends throughout life who had down right horrible qualities about them (cheaters, liars, manipulative and gold diggers). Outer beauty doesn’t mean someone is better than you. No one is better than you because of their looks period!

 

Flirting just takes practice. Luckily for you, you work in retail and can practice interacting with people every day.

[Inflikted]

You’re in luck my friend, you ‘re in the perfect industry to practice flirting.

 

I guess, but I've been in retail/ service for, like, 8-9 years, and I don't feel I've really gotten any better at being "social". Of course, I have my "professional" front that I put on to help people and properly do my job, but that's not super helpful for actually connecting with and having relationships with people.

 

To me, flirting is all about being authentic, warm and making the other person feel comfortable. Making a girl laugh is always a plus! If you’re able to throw in some natural witty banter you’ll be golden (again this take practice to not come off as fake).

 

Well, what separates "flirting" from a normal, upbeat, friendly interaction?

 

The thing that I feel... I dunno... "self conscious" about, I guess, when it comes to "flirting" and dating is that flirting leads to dating, and dating, well, eventually, dating leads to sex. So, in a way, to me, I feel like by "flirting" with someone and trying to date them, I'm basically saying "Hey, I'd like to eventually have sex with you", and it makes me uncomfortable to imply that to someone else.

 

Heck, honestly, I find the whole idea of sex and intimacy to be overwhelming and a bit nerve-wracking, and dating seems daunting to me because if I'm going to date, eventually I'm going to come to that "hurdle" at some point.

[preraph]

Think of it as something that you'd do for yourself and not for others. You may just be surprised how good it feels. Don't think of it as a chore, but rather an investment in yourself.

 

 

 

Then take your head out of the game. I was an awkward teenager at 17, and I remember a girl at a party asking me three times (bless her heart) to leave the party and go stargazing with her. I responded that the light pollution was pretty bad in this part of town. I was so wrapped up in what I thought I should do, and who I should ask out, that I completely overlooked the obvious.

 

That's priceless.

 

Where I grew up boys were all mean little boys, so I was very nervous with guys even up into high school. I had a huge crush on one and he probably caught wind of it and offered me a ride home one night and stopped to get an iced soda first at the drive-in, and he drove real slow on the dirt/gravel road back to my house (where people sometimes parked) and I was so nervous my hands were shaking and the ice was rattling in the cup. It was so embarrassing.

[Gillys]

 

 

Well, what separates "flirting" from a normal, upbeat, friendly interaction?

 

The thing that I feel... I dunno... "self conscious" about, I guess, when it comes to "flirting" and dating is that flirting leads to dating, and dating, well, eventually, dating leads to sex. So, in a way, to me, I feel like by "flirting" with someone and trying to date them, I'm basically saying "Hey, I'd like to eventually have sex with you", and it makes me uncomfortable to imply that to someone else.

 

Heck, honestly, I find the whole idea of sex and intimacy to be overwhelming and a bit nerve-wracking, and dating seems daunting to me because if I'm going to date, eventually I'm going to come to that "hurdle" at some point.

 

I see where you're coming from...I think what separates "flirting" from a normal, upbeat, friendly interaction is the mutual attraction. If a girl is into you, your normal upbeat friendly interaction is probably going to be seen as flirting IMO.

 

Maybe try thinking of dating as something fun and making another person feel comfortable rather than a goal for a relationship and sex. It would probably take some of the pressure off so you can get more practice and until it feels more comfortable. I wasn't allowed to date way back in high school so all I could do was flirt. I dont think I ever had any pressure with flirting because I knew it wasn't going to go anywhere as my dad would've probably killed any boy who showed up at my house haha.

 

Have you heard of Corey Wayne? he has a book and youtube channel. I dont agree with everything that guy writes (as it is mostly written for dudes) but he does give insight for men trying to learn how to interact with women, pick up on subtle details in flirting, communication, etc.

[todreaminblue]

cptinsano wrote about being able to hold a conversation first with friends this is so true,as is the fact flirting is a different sphere a more advanced interaction......

 

 

...conversations that are comfortable and easy should be your first goal...stop seeing woman as being out of your league and see them simply as women no pedastals...be open be respectful and friendly maintain eye contact.....and do it often...practice...with all ages all types of people not just women......conversations that flow often lead to flirting when there's interest.....

 

 

join a group like toast masters...get used to speaking in public places....build your confidence in your own voice..... and also your knowledge base....of current affairs....and or passionate topics you love to talk about.......and realize you have something to say that is as worthwhile as the next person......practice...wherever and whenever you have the opprotunity too..introduce yourself to people you dont know .....ask them how their week is going...pretty simple start....works wonders

 

and you will notice you will start to pick up on cues....because not only speaking but becoming soemone who listens to conversations not just hears them will happen also........deb

Edited May 17, 2017 by todreaminblue

[normal person]

Well, what separates "flirting" from a normal, upbeat, friendly interaction?

 

Sexual tension. You can have one conversation with a person and it will be completely platonic. Have the same conversation with another person and look at them differently, position your body differently, use a different tone of voice, react differently, etc -- now it's a whole "different" conversation. Lots of communication is non-verbal.

 

The thing that I feel... I dunno... "self conscious" about, I guess, when it comes to "flirting" and dating is that flirting leads to dating, and dating, well, eventually, dating leads to sex. So, in a way, to me, I feel like by "flirting" with someone and trying to date them, I'm basically saying "Hey, I'd like to eventually have sex with you", and it makes me uncomfortable to imply that to someone else.

 

But if someone is flirting with you, they're basically subconsciously entertaining the idea of the idea of having sex with you. If they didn't like the feeling, they'd stop or go away from you. They're willing participants.

 

Also, consider that it's par for the course to desire relationships and sex. It's a biological urge. It's honestly more off-putting to a woman if she tries to flirt with you and you're visibly uncomfortable rather than if she tries and you reciprocate. If you shy away from an advance, she's going to think "Why is this grown man turning down a opportunity to talk to a woman and potentially date her and have sex? What's wrong with him... or me?" If anything, that should make you more uncomfortable than the implications of playing along with it. If she's flirting with you, she's showing vulnerability, she wants you to like it. Getting you to at least think "Hey, I'd like to have sex with you" is her goal. Women want to be desired and pursued. You shying away from that represents failure on her part, or a knock on her as a viable partner, and/or your inability to partake in the little mating dance and therefore reproduce. Neither is what you want.

 

If I were you, being that concerned about the implications of the interaction to someone else, I'd be way more open to conveying the message that I'm comfortable with the idea of potential dating/sex -- doing the opposite is what's going to make her uncomfortable. Whether or not that makes you comfortable is a different story. If that's not the kind of thing you can do, you should probably talk to a professional about it. I guess it depends on which discomfort you'd rather have. That which you put on her by rejecting her advances, or that which you put on yourself by accepting them. I think if you want to progress, you'll need to learn to deal with the second type of discomfort because if you conquer it, it will ultimately lead you closer to what you want.

[GunslingerRoland]

Flirting ranges from being friendly, to sexual innuendo like some have said. It sounds like this was pretty light flirting. So the keys to that are being positive, smiling, open posture, complimentary. If she was buying something you could have said, great choice, this "item" suits your, or something, but it should be genuine.

 

Tread lightly on moving towards the more sexual innuendo type of flirting unless you are sure it's wanted, especially in a workplace situation.

[Miss Peach]

IME women will often show a lot of eye contact, smile, touch (i.e., tap your arm), act happy to see you, are comfortable being in close physical proximity, etc.

 

I've also found a lot of women but not all drop clues into the conversation such as getting out of a relationship, needing to go somewhere (you could take her to), etc.

 

If I get sexual innuendos early on from a guy then I think he's looking for a hook up so proceed with caution there. But things like nice shoes, nice necklace, you're gorgeous, etc. can be used but remember women are used to hearing these things so it give up that you're interested.