Derek Flint
Master Don Juan
- Joined
- Nov 24, 2002
- Messages
- 1,737
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Usually I don't ask for advice but there's this one girl that I'd like to date.
Here's the basics:
I'm 57 but look about 45
(Photo attachment below)
This girl is early to mid 30's, smoking hot and her personality is as good as her looks.
She's not the kind of girl that goes to clubs or other BS and has a good head on her shoulders and has her **** together.
Kind, sincere, unpretentious, genuine...the total package.
GF material.
I run into her here and there and we have short but good conversations.
She tells me what's going on in her life.
Things like about making a career change, taking classes to fulfill that goal and even her current living situation for example and has indirectly complimented me a few times.
Example; "You're getting very tan. It looks really nice."
She will be very open about herself and has revealed a lot but never mentioned a BF, but I don't know if she's interested or if it's just how she is with other people/guys.
Other times, she can be inattentive towards me.
Typical woman, right.
I'm going to ask for her number since our conversations are mutually enjoyable but my concern is that she's just a friendly, outgoing girl and might not be interested.
If she says something like "Oh, I like you but..."
Should I try to flip the script and respond with something like "Hey, that's not where I was going with this.
I don't know you well enough to have even considered that"
And/or: "Besides, you're way too young for me" (In a more diplomatic way and to make her prove to me she isn't.) or is there a better response to peak interest?
I'm at a bit of a loss here because at times it seems like she's interested but at other times not.
And yes, I do have a bit of "one-itis" for her because she's a definite keeper and I like her a lot as I really enjoy talking with her but would like to escalate but it's difficult when I only run into her randomly once or twice a week and we're both on our way to other places.
This one has got me stumped.
Should I try to build more repoire/rapport and risk losing her to some other guy who knows her better/has more "access" to her, or just ask her out?
Note that it took some time just to get her to engage in conversations with me so I sense she might have trust issues or just needed some time to figure out that I wasn't just another guy trying to hit on her as she, like all hot women get that all day every day.
I know the first thoughts will be to just ask her out and I'm pretty sure she will.
OTOH, I sense she needs more time to build comfort/connection but as mentioned, I have limited ability to do so as our paths do not cross very often.
I don't want to f*** this up as she's a keeper and I have to play it right.
I realize she's likely decided already if she would or wouldn't, but I don't want to be like every other guy that hits on her.
If she is interested but undecided, how can I "flip" her or move things forward if she says "I like you, but..."?
Apologies for not giving a better description of the situation, but I'm posting this from my cell phone and not a keyboard.
Right now, I'm in a good place mentally and physically and it won't be the end of the world if she says "no" but OTOH, she is a definite keeper.
I know I'm overanalyzing/overthinking this, but I don't want to f*** it up and if she capitulated, I want to try to salvage things in case I'm moving too fast for her.
I've probably had 6 brief but revealing conversations with her so this situation is hard too read.
Here's the basics:
I'm 57 but look about 45
(Photo attachment below)
This girl is early to mid 30's, smoking hot and her personality is as good as her looks.
She's not the kind of girl that goes to clubs or other BS and has a good head on her shoulders and has her **** together.
Kind, sincere, unpretentious, genuine...the total package.
GF material.
I run into her here and there and we have short but good conversations.
She tells me what's going on in her life.
Things like about making a career change, taking classes to fulfill that goal and even her current living situation for example and has indirectly complimented me a few times.
Example; "You're getting very tan. It looks really nice."
She will be very open about herself and has revealed a lot but never mentioned a BF, but I don't know if she's interested or if it's just how she is with other people/guys.
Other times, she can be inattentive towards me.
Typical woman, right.
I'm going to ask for her number since our conversations are mutually enjoyable but my concern is that she's just a friendly, outgoing girl and might not be interested.
If she says something like "Oh, I like you but..."
Should I try to flip the script and respond with something like "Hey, that's not where I was going with this.
I don't know you well enough to have even considered that"
And/or: "Besides, you're way too young for me" (In a more diplomatic way and to make her prove to me she isn't.) or is there a better response to peak interest?
I'm at a bit of a loss here because at times it seems like she's interested but at other times not.
And yes, I do have a bit of "one-itis" for her because she's a definite keeper and I like her a lot as I really enjoy talking with her but would like to escalate but it's difficult when I only run into her randomly once or twice a week and we're both on our way to other places.
This one has got me stumped.
Should I try to build more repoire/rapport and risk losing her to some other guy who knows her better/has more "access" to her, or just ask her out?
Note that it took some time just to get her to engage in conversations with me so I sense she might have trust issues or just needed some time to figure out that I wasn't just another guy trying to hit on her as she, like all hot women get that all day every day.
I know the first thoughts will be to just ask her out and I'm pretty sure she will.
OTOH, I sense she needs more time to build comfort/connection but as mentioned, I have limited ability to do so as our paths do not cross very often.
I don't want to f*** this up as she's a keeper and I have to play it right.
I realize she's likely decided already if she would or wouldn't, but I don't want to be like every other guy that hits on her.
If she is interested but undecided, how can I "flip" her or move things forward if she says "I like you, but..."?
Apologies for not giving a better description of the situation, but I'm posting this from my cell phone and not a keyboard.
Right now, I'm in a good place mentally and physically and it won't be the end of the world if she says "no" but OTOH, she is a definite keeper.
I know I'm overanalyzing/overthinking this, but I don't want to f*** it up and if she capitulated, I want to try to salvage things in case I'm moving too fast for her.
I've probably had 6 brief but revealing conversations with her so this situation is hard too read.
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