There's a guy I want to meet but am nervous to approach him. Advice?

He works at my daughter's school. No wedding ring. I've been eyeing him for a long time. How do I meet this guy? He's not a teacher. I see him briefly when I'm dropping her off @ school. I'm always in my truck and he's directing traffic/providing security.

I want to meet him badly but am terrified that I'll look like an ass. She'll be going to this same school for the next 7 years so would have to see him on occasion. Help! :)

Where's my girl @Redeyemindtricks to chime in?


Most Helpful Guy

  • Park a bit away and walk your daughter the rest of the way. When he has a moment, approach him and tell him you have noticed him many times and want to meet him. A bit forward? Yes. A little risky? Only a very little. I would be open to someone approaching me like that, and if she was as good looking as you, and with a great personality that you seem to have, I would jump at the chance to get to know you better. The worst that could happen is if he is "taken", but if it were me I would still be flattered and would not embarrass you at all about me already being taken. (I would tel you, but in a very nice way and hope we could still be friends.)


Most Helpful Girl

  • Soooo I don't really know what yr default personality is like, in terms of making random flirty comments and so on. Because I don't, I'm pretty much just grasping here --- but, I'll try.

    I always like to... make fun of people a little bit, if I can. Not in an actual sardonic mocking way, of course -- just in a good-natured way.
    Does he have to wear one of those reflective safety-vest thingys?
    If so, you could totally use that as a conversation piece ahah... "I never thought I'd live to see the day when someone makes THAT thing look good", or something like that.

    This is better than just saying something like "I wanted to come over here and introduce myself", or whatever, because it's not AS direct.

    See, if you are TOO direct about this sort of thing, there are 3 things that could potentially go wrong:
    You may just come across awkward af. I mean, you're ALREADY nervous -- I can only imagine what the pressure of a *direct* approach would do to that.
    If he's the more traditional type of guy who wants to *feel* like he's making the first move, then, you wouldn't want to take that particular card out of his hands. If you do, he might just... not know what to do.
    Unfortunately for the rest of us... A LOT of women who DO make those kinds of super-direct approaches also happen to be, well, very manipulative in general. At his age, this dude certainly has SOME kind of history with women -- and if he's had the bad luck to come across a master manipulatrix who DID make all the moves first, he's going to be forever shy about women who are too direct.

    If you make a comment like the one I put up there ^^ instead, then you're minimizing these problems.
    He can still FEEL like he's making the first "real move" when he responds to you (even though we all know the truth ahah)... and it's not the sort of thing that he'll find off-putting if he's that type.


    Also -- you reallyreallyREALLY shouldn't linger too long with the whole staring thing.
    That's probably not as weird as it would be the other way around (if some guy spent weeks or months side-eyeing us without actually saying anything)... but, it's still gna get weird. I'm sure the guy is not totally oblivious.

    In other words, you should actually DO something, before things have a chance to go "stale". (And because you need to get fucked into another dimension.)

    G'luck babes <3 <3

    • @Redeyemindtricks

      Ahh yes. Was waiting for your reply.

      I haven't been necessarily staring @ him cause I'm always in my truck dumping off the kiddo in front of the school and sometimes he's there. Today I had to go into the office and he was in there shooing some kids who were hanging out in there to go outside. That was the first time I think we ever looked at one another (not sure if he tecgonizes me when I'm in my truck). I was too far away to say hello or anything.
      He doesn't wear a silly vest. As a matter of fact, I love the way he dresses (jeans & flannel-type or button down shirts). Too bad in a way cause that would've been a great ice breaker. His other job is VERY similar to mine if u know what I mean but I can't bring that up because I found out via stalking his LinkedIn page. Haha. So I gotta find another way to approach him without it being weird.

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    • "ugh"
      ^^ you spelled #mmhmm wrong <3 <3

      Go get him gurrlllllll oh yeahhhh

    • Hehe. Thanks for the motivation! 😘


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What Guys Said 17

  • Seriously? You are like PRIME 'MOM' for a divorced, or single guy!!
    SHt!! I want to meet you!! :)
    How isn't it TOTALLY OBVIOUS to you? Wear a VERY short skirt, and a low-cut top, a pretty, lacy bra, that shows, because you 'forgot' to button the top three or four buttons!! Then, when you drop her off, do something you KNOW is wrong!! Get in the wrong lane, or the wrong place!
    He will come over, and tell you, if he is any good at this menial job, and you can just talk to him!!
    If he isn't into the lace, and curves, and how you flirt, maybe he 'bats on the other team?'
    Come on!! You are in your PRIME!! Use what you have and flirt, and play!!
    I KNOW there is an age-exclusion from the 'slut' definition, for the over 40, hot, seductive woman with a daughter!!
    Just talk to him like a person!! Don't think it up too much, and confuse yourself!! Flirt, and be yourself, even if that is something awkward, but delightfully endearing!!

    • This would be a good idea... if life were porn, and if porn were life.

      But, life β‰  porn, and porn β‰  life. Therefore, this is actually a terrible idea.

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    • @redeyemindtricks dammit! You haven't solved that dilemma yet huh? Despite being a professional in my work life, I'm a complete 12 year old a lot of times!

      Love the meme ( or whatever it's called) there too! Ha! 😘

    • If @Redeyemindtricks told you, she'd have to kill you. Sorry man!

  • Just do it, go to him and say what you wanna say. Think that if you don't do it you'll regret later and wonder what would've happened if... you won't wanna feel this kind of regret.

    Do it, the worst think that can happen is rejection and given the situation it won't be that bad.

    • I'm just really apprehensive as it might be embarrassing if he's taken and I gotta see him often when dropping off my daughter. Perhaps if he doesn't know what I drive it'll work, haha.

    • Sometimes embarassing situations are part of the whole think. I think that it's worth the risk. Awkwardness ends, regret is more painful.

    • This is true!

  • You have to think about the school protocol. He would probably get in trouble socializing with a parent, and the school gossip mill would be torture for your daughter.

    • Ehh, not too worried about that. I know how to be discreet. Plus, we have a couple things in common. I think this is his side job. What he really does for a living, I'm involved in it as well and it requires a lot of down low kinda stuff so I think I can handle that part. Thanks for your input!

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    • This is true but thank god he's not a teacher and this is a side job for him so he's not around all the time. That's the best I can do I guess *shrugs*

    • Still might be trouble...

  • Stop eyeing and start talking to the man firstly. You won't look like an ass. If you flat too much and pretend you are someone you aren't then yeah maybe you will lol. Just walk your daughter into school one day. If he's free talk to him. I am such and such this is my daughter. I don't think we've had the pleasure to meet.

    • Thank you for the advice! Duly noted!

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    • You always seem very sincere in your answers and very thorough too, I might add. I like it!

    • Well im glad you do! 😊 thanks

  • Just do it & be direct , as a woman , you will not risk a nasty rejection , like a lot of men often receive from women. Men are rarely , if ever , seen as desirable , so he will be flattered. Men are crap at reading the subtle female signals , simply because our brains are wired so differently , it may be obvious to a woman , but invisible to a man.

    • Wow, this is very interesting. Men don't feel like they're desired? That floors me.

      Thanks so much for the insight into male's thinking! I've learned something today. 😊

    • Men have been bashed , demonized & basically painted as below excrement for decades by the " media " & the feminist ( feminazi ) movement for decades , more intensively in the last 20 years or so , you can't deny that male sexuality is viewed as predatory , disgusting , perverted & all out wrong , no wonder men do NOT feel desired in general. Have a read of this blog post , see what you think

  • My big piece of advice is to talk to him when your daughter isn't around. Drop her off, wait for foot traffic to die down, and invite him for coffee. Especially if he's noticed you around in your truck at all. The forwardness can catch us (guys) off guard but it also removes any of the doubt as to whether or not you're interested (which is usually our biggest hurdle). Go to it!

    • Thank you for this. Sounds like sage advice. Appreciate it!

  • Are you a truck driver? Anyway irrelevant. What I suggest is walk your daughter to the gate so you have to walk past him. Just make greeting gestures the first few times and then build up to small talk and let the ball gather snow.
    Glad to have helped.

  • Go and talk to him. You can throw in that you're glad that you can feel safe about your daughter when he works there...

    by the way why are you affraid, I see no reason why would he reject you. go for it!

  • just do it, he's not going to approach you.

    • Thank you, so true. I'm always in my car and he's standing out front of the school and I can't dilly dally around cause there's a line of cars to drop kids off!

  • I say go for it.

  • Have your daughter find out who he is. How do you know he isn't a teacher?

    • Hahaha! I asked her today as he's the only "campus supervisor" on the roster. She didn't know who he was. She's still young so prob doesn't pay attention to the adults too much. 😊

    • I know he's not a teacher cause I looked up the staff on the school's website. More often than not, schools have their staff listed on their webpage.

  • I think you should ask him...
    You are 44? It is so MILF

  • If you really like him so just go for it. Guys like when girls hit on them I would :D

    • Well I just want to meet him, not necessarily hit on him @ the school lol. Just trying to get the nerve up and the opportunity to make that happen.

      Thanks for the insight too on what men like! πŸ˜‰

  • Just casually talk to him about what's going on around y'all

  • Just go for it honestly. You really have nothing to lose so good luck!

  • Amazing how you never even considered that this man might not want you invading his personal space like that. What makes you think he owes you his attention?

    • Ehh... did I ever imply I expect his attention? I'm pretty much implying the OPPOSITE. Did you even read my post?

      I'm saying I'm nervous as hell because I'm afraid (almost expecting) he'll reject me hence the reason for the post at all. I even said " my daughter is going to this school for the next seven years and I'm afraid to look like an ass"

      I don't expect jack shit from him. Where the hell did you come up with your answer to my question?

      How is simply meeting a person an invasion of space? It's not like I'm barging in on a dr performing a heart transplant or something.

      Perhaps you aren't used to folks even interacting with you socially. I said I want to meet him. I didn't say I wanted to marry him or anything. Jesus h Christ πŸ™„

  • if he's a security guard, he's being paid to be nice. just be careful with this

    • No not a security guard but more of a yard duty type thing.

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    • True, I get that but I've not even talked to him ever at this time. Who knows? He might be a total douchebag and not even worth my time. I want to meet him though.

    • he wouldn't be a security guard, if he was a douchebag, he obviously got the job because he was a charmer

What Girls Said 3

  • Awesome! 7 years is a long time to form a relationship, be a couple and hell maybe get engaged? πŸ˜› But honestly I would try and find a time where he is by himself and has some free time. Walk your kids to school and casually start saying hi and how are you. Then when you figure out a time where he has free time by himself strike up a conversation with him. About anything really; share an opinion about security of the school since he works with security he will be more likely to give you a good response. After a little talking introduce yourself and say that your kids started school here. Also dont be afraid to compliment him because he will immediately get the impression that your into him and things will go a hell of a lot quickier if you didn't.
    Just keep talking to him every once in a while and wait for him to ask for your number 😊

    • Thank you! I'm a little rusty in the dating game nowadays. Used to be so easy for me, haha.

      Great suggestions, thanks!

  • If it were me, I'd just go up to him and ask about something mundane, just to make small talk. The next time you see him give him your number

    • I'll definitely consider that. Thank you for the advice! 😊

  • From a teenager perspective (which I'm assuming your daughter is in her teens or close to them) I would be mortified if my mom dated someone who worked in the school. I'm sure she would feel the same way especially around middle school age. Imagine all the girls who would make fun of her.

    • Perhaps. But who's to say that this guy would even be interested or is even single?

      It may seem a little weird but hoping the fact he's not there full time nor a teacher will be of less a concern for her.

      I also don't socialize with any of the school parents or staff ( not because they're bad people--I just work full time and don't hang out there) I simply drop her off in my vehicle or I may go to a parent/teacher conference twice a year and I'm out.
      99.99% of the people there have no clue as to who I am.

      I appreciate your input, thanks for answering.

    • Well but especially in middle schools and high schools staff get involved with the students not just the teachers. At my school our campus supervisors who help run parking and stuff get to know the students really well. So for the sake of your daughter I would just pass on this guy. Like I said, if I were in your daughters shoes I would be totally mortified.

    • I get what you're saying and thanks for the insight.