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I'm 40 and friends with a guy who is 21. Our families have been friends for generations and there is nothing one wouldn't do for the other. During the past year, our roles evolved from "family friends/acquaintances" to "close friends" to "confidants who can literally talk about anything." I treasure the friendship and don't want to mess it up for all the world. What I haven't told him is that I am falling hard for him. Last night, we were having innocuous conversation about dating. He was talking about wanting to have a girlfriend and what qualities he's looking for. After talking to me about his previous attempts at relationships, he told me that I was beautiful and he loves talking to me (that it makes time fly), but that we could never go out as more than friends because it would be too weird (conceivably because of the family connections). Was he testing the waters for my reaction to the possibility or just finding a nice way of telling me I shouldn't apply for the position?

2006-10-04 05:53:52 · 7 answers · asked by Cleveburgher 3 in Family & Relationships Singles & Dating

Wow! In analyzing the responses received to date, I found it interesting to see that guys interpret my friend's behavior one way and the girls see it the other way. (Additionally amusing is that, when respondent gender was not apparent, the answer was non-committal one way or the other.) There must be something to the Mars-Venus thing! Thanks for the valuable feedback and a good chuckle in the process...

2006-10-05 02:18:37 · update #1

7 answers

i think that it was telling you that he has atleast thought of possibly going out with you. It is near 50/50 if he was trying to get a reaction, or just being honest about it. But it is worth a try, just have a talk with him about it. it seems like you're open and that he would completely understand since he has atleast thought of it.

2006-10-04 05:59:20 · answer #1 · answered by David 5 · 0 0

I'd say play it by ear. You don't want to jump into anything because of the families involved, not to mention that the age difference will no doubtingly cause conflict.

If he pursists about the relationship, then go on a date, see if it's something your into. But take things SLOW. That's for your own safety. Protect your heart.

2006-10-04 05:58:09 · answer #2 · answered by Anonymous · 0 0

I think he was nicely telling you not to apply. Guys typically say what they mean (though not always). If you have had a lot of conversations about what it would be like for you two to date, I'd say you might have a chance. But, with him being younger, he may care more about what others think, esp when it comes to family.

2006-10-04 05:57:13 · answer #3 · answered by Angel Baby 5 · 0 0

don't apply!!! if theres going to be any applications handed in, let it be his.
On another note I'm not one for pointing things like this out but isn't 40 vs 21 a little steep (considering maturity and experience n all that)?

2006-10-04 06:01:26 · answer #4 · answered by ? 3 · 0 0

Probably telling you like it is without letting you down. Girls have a way to inadvertently tell how they feel without really knowing they did so. So, he has probably picked up on signs that you like him, and this is his way of plainly stating that nothing can come of this...

2006-10-04 05:56:22 · answer #5 · answered by Angel Eve 6 · 0 0

He was testing the waters and would like to have a Clandestine
affair with you.......

2006-10-04 05:57:14 · answer #6 · answered by RiverRat 5 · 0 0

He's feeling you out as you already figured out. You got to decide for yourself whether to proceed.

2006-10-04 05:57:03 · answer #7 · answered by Cary Grant 4 · 0 0

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