FrustratedGuy91 Posted March 28, 2014 Posted March 28, 2014 Sooo this has never happened to me before. There's this lady that manages my family's cars insurance (She's an insurance broker). I run errands for my family so I usually go pay the insurance bills to her office. Most of the time her secretary is the one that deals with me but on occasion she's not there so this lady is the one that takes my payments instead. Today was one of such occasions. Now I don't wanna sound disrespectful but she's pretty much a milf, anyway at some point we were talking and I mentioned that I drive one of the family's cars and she said something like "Oh you should definitely have my number, then. In case you need anything". I may be young, but I can tell by the way she said it, that this wasn't merely her being professional. Furthermore my aunt had to call her because she forgot to give me an important paper and when she asked me to go back to get it, the insurance lady mentioned how I was "cute" and my aunt jokingly replied something like "I know, right. I don't know why he can't find a girl" and apparently this lady's reply was "Well, I gave him my number" So, what do I do? I've never been in this situation before so I'm completely lost. PS (She's like 40 but attractive; I'm 23)
Author FrustratedGuy91 Posted March 28, 2014 Author Posted March 28, 2014 Go for it! Yeah but how?! Should I.. I dunno text her something? I have no idea what to do. (Also I was thinking back, my whole family has her number and she knows it, so there was no professional reason for her to give me her number)
GoreSP Posted March 28, 2014 Posted March 28, 2014 Yeah but how?! Should I.. I dunno text her something? I have no idea what to do. (Also I was thinking back, my whole family has her number and she knows it, so there was no professional reason for her to give me her number) Just call her to ask her out for a drink. Then flirt your ass off and enjoy the rest of the evening. I'm 33 and was contact by a 22 year old not too long ago. I didn't think there would be anything serious between us - but man did we have fun together....if you know what I mean 2
Author FrustratedGuy91 Posted March 28, 2014 Author Posted March 28, 2014 Just call her to ask her out for a drink. Then flirt your ass off and enjoy the rest of the evening. I'm 33 and was contact by a 22 year old not too long ago. I didn't think there would be anything serious between us - but man did we have fun together....if you know what I mean Yeah I've figured she doesn't want anything serious, neither do I. But what if I misinterpreted what she did? I'm kinda afraid of messing up.
RonaldS Posted March 28, 2014 Posted March 28, 2014 Call her. Say you have a question about collision coverage and then ask her what would happen if you 'rear-ended' her. 7
Jordvn Posted March 28, 2014 Posted March 28, 2014 get it wet. no problem in a coug hunting down young meat.
Author FrustratedGuy91 Posted March 28, 2014 Author Posted March 28, 2014 Call her. Say you have a question about collision coverage and then ask her what would happen if you 'rear-ended' her. LOL I wish english was the language spoken in my country haha Seriously, though. I'm kinda shy for starters I usually ask a girl out when we have some common context or by mere luck. I need precise instructions for this one.
Hello_is_it_me Posted March 28, 2014 Posted March 28, 2014 Call her. Say you have a question about collision coverage and then ask her what would happen if you 'rear-ended' her. lmao love this 1
GoreSP Posted March 28, 2014 Posted March 28, 2014 Call her. Say you have a question about collision coverage and then ask her what would happen if you 'rear-ended' her. LOVE IT!! Seriously OP just call her.
Author FrustratedGuy91 Posted March 28, 2014 Author Posted March 28, 2014 LOVE IT!! Seriously OP just call her. And? She'll be like "Can I help you with something?" And then what? do I drop a one liner? haha. Besides she gave me her number a couple of hours ago, shouldn't I at least wait? Wouldn't it be better to text her with an excuse like IDK if she knows any good repair shops to fix one of the cars or something like that?
GoreSP Posted March 28, 2014 Posted March 28, 2014 And? She'll be like "Can I help you with something?" And then what? do I drop a one liner? haha. Besides she gave me her number a couple of hours ago, shouldn't I at least wait? Wouldn't it be better to text her with an excuse like IDK if she knows any good repair shops to fix one of the cars or something like that? Just tell her you feel like going for a drink and ask her if she wants to join you. She didn't give you her personal number for professional reasons 1
gaius Posted March 28, 2014 Posted March 28, 2014 Call her up and tell her you want to take her to dinner and a movie next weekend. Or whenever you have some free time. But have a specific date/time in mind and resteraunt picked out. You can always change it if there's an issue but most women like the guy to manage that. Don't force her to do it.
Author FrustratedGuy91 Posted March 28, 2014 Author Posted March 28, 2014 So basically I ask her out like I would a woman my age?
Hello_is_it_me Posted March 28, 2014 Posted March 28, 2014 so basically i ask her out like i would a woman my age? -__- yes!!!!! 3
Armegoggon Posted March 28, 2014 Posted March 28, 2014 Just call her anyways and make a decent conversation. Take advantage of this opportunity.
gaius Posted March 28, 2014 Posted March 28, 2014 Yes. The dynamic doesn't change because shes older.
jay1983 Posted March 28, 2014 Posted March 28, 2014 Hang on a minute, I love the comments everybody posted. Especially the one about rear ending her! LMAO Don't you guys thinks he should send a few texts first just to feel this out? I'm not an expert, but I do think I'm right about this. I say send texts that have nothing to do with work, cause if you ask her some s**t about insurance, she answers your questions and your still left wondering. Send a mild flirt, just to make sure you didn't misinterpret this whole thing. Incase if you've got the wrong idea, you can just say "I was just being friendly" Can anybody back me on this?
gaius Posted March 28, 2014 Posted March 28, 2014 It's fine to wait a few days if you want but don't phumper around with excuses like finding a good repair shop. You have her number so go straight for the jugular and ask her out. And if she seems hesitant for whatever reason or wants to be friendd don't buy into it. Tell her you want a date with her.
GorillaTheater Posted March 28, 2014 Posted March 28, 2014 Can anybody back me on this? Nope. I'd plunge in head-first (so to speak) and ask her out. What the hell, right? You get a little older, and you learn to appreciate the direct approach.
jay1983 Posted March 28, 2014 Posted March 28, 2014 Nope. I'd plunge in head-first (so to speak) and ask her out. What the hell, right? You get a little older, and you learn to appreciate the direct approach. If she's interested, she'll flirt back. Then that's a better time to do what your saying.
Grumpybutfun Posted March 28, 2014 Posted March 28, 2014 Even if she meant insurance, she might either find it flattering or amusing, and that isn't such a bad thing. Close out the rejection with, you're very beautiful so if you have a niece my age I'd love to meet her. Some of my most memorable sexual experiences as a twenty year old was with older women who were much more verbal and enthusiastic in bed. Just also be aware that if you "date" this situation with a more mature woman with baggage will come with its own special challenges. Hey, but some women are worth challenges being overcame. Call her and be direct, as GT said. Possibly say, I really enjoyed speaking with you at your office, I would love to take you to dinner one night to get to know you or take you line dancing or see a hockey match or whatever.....don't overthink this or be afraid of rejection. Rejection is just a part of dating and the sexual dance. Have fun, Grumps 2
Stay Posted March 28, 2014 Posted March 28, 2014 In my opinion the part where she said "Well I gave him my number" is pretty much a given, she means something. OP we told you to just ask her out for drinks or something already... You cannot ask us how to do it, etc. just do it. We're not going to guide you through the whole thing so you just need to do it and go with whatever happens. 1
jay1983 Posted March 28, 2014 Posted March 28, 2014 Close out the rejection with, you're very beautiful so if you have a niece my age I'd love to meet her. Grumps This is good, I say go with this.
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