A
female
age
26-29,
anonymous
writes:There is someone who I would like to spend time with and ask if they would be up for meeting me to get to know me .this may seem really easy for some people but for me it isn't . up to now its the first time ive really ever wanted to see if I could have the same interests as someone or perhaps have the confidence just to say hi , fancy meeting me for a coffee or something however I just still haven't done this yet mainly because I feel this person would be alarmed or find it unusual for me to feel this way .ive been reading some people's view on whether there is something wrong with having older friends as this person is older and most of the views on this site suggest there isn't and some posts explain the age differences and reasons why they are friends with older people . I think in my case I just think this person would think , why do I want to be friends with you.being upront would be best solution and I would having nothing to lose if I told this person that ive been wanting to talk to you more . but I would find it hard to put myself out there and to worry about possibly being rejected.Ive only had brief interactions with the person I want to get to know better,but I think it would embarrass me Being direct about my desire to . Casually let them know that id be happy to chat again or get together in a different context (e.g., “Hey! I really enjoyed our conversation! Any chance you’re open to grabbing a coffee sometime?” or “ I’d love to find a time to hang out and maybe go for a walk together!”). what shall I say , as its been on my mind a while and something will only go off my mind once ive done something about it .
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female
reader, OldSoulGirl  +, writes (20 August 2019):
I know I also responded to a similar post at least more than once and I also feel like you’re the same girl. At this point, it’s an obsession. Stay away from this man period. You sound like you’re in like with your idea of this guy. Stop coming here asking the same questions if you’ll just keep ignoring our advice. You’re obviously too immature to date someone older if this is how you act.
Why do you keep asking the same question? I’ve free;y had discussions with people older than me. I’ve never come online constantly begging for advice about doing it or not. Why do you need validation? I find it a little concerning at this point. I don’t know if you’re just trying to troll or you’re an inexperienced girl incapable of approaching people herself.
Seriously don’t do this to yourself. Work on your self-esteem more than anything.
A
female
reader, CindyCares  +, writes (20 August 2019):
 I think you posted the question linked by YCBS, and also another one, or more, in which you gave a slightly different version of the events. I.e. you did email him ( or text him ) that you wanted to get to know him, and he answered, rather curtly, " What do you want to know ? ".
That sounds rather like a brush off to me, and apparently he is not keen for you to get to know each other . So I'd certainly leave him alone.
Then again, - it seems to me that you are starting to be slightly obsessed by your wish to " get to know " this guy, whatever this may mean to you . Obsessions must be resisted and reined in; but … if you find it impossible to accomplish it , then they must be indulged :). So go ahead, and write to him. One letter or more, at your heart content. UNLESS- this guy is married , or he is your teacher, or your boss at work, or your pastor- or in any other position in reference to you , in which even a casual, friendly approach may be misconstrued and make things awkward for him just because of being very unusual, or contrary to the policy of his workplace ( or Church/ association / organization , you get the concept ). In other words, it's not all about YOU and what YOU want and prefer. You have to take into account also the other party's preference, position and sensitivities.
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A
male
reader, anonymous, writes (20 August 2019): OP, I remember the last time that you were here asking about this older man. I think it is obvious that you want to hook up sexually with this man. You kind of sound like a creepy stalker kind of girl. If this man is married, then get over it! If he is in a committed relationshp, then get over it! If he is a pastor, priest, teacher, doctor, dentist, your boss, or coworker, just let it go! You are trying to fish in dangerous waters! You are most likely too immature to have anything truly in common with an older man. The fact that you keep asking this question, speaks of your lack of maturity. Have you considered counseling, to help you deal with your lack of confidence and your indecissiveness? If you went into counseling, your counseler could explore the pros and cons as well as potential risks in trying to contact the man who you are obsessing over. Please do not cause trouble in a marriage by inserting yourself someplace where you do not belong!
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A
male
reader, Fatherly Advice + ♥, writes (20 August 2019):
 I agree 100% that with you "something will only go off my mind once ive done something about it "
You keep asking the questions and you keep thinking about it, and you keep failing to DO anything about it.
My advice is to go forth and DO. Sure it's risky, and you might find a creep instead of a sugar daddy, but without going to the effort of creating a profile here, you simply are not going to get the kind of attention you crave.
Since I'm neither a creep nor a sugar Daddy, this will be my final reply to this oft repeated question.
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A
female
reader, Youcannotbeserious + ♥, writes (19 August 2019):
 Suspect you are the same person who posted THIS:
http://www.dearcupid.org/question/id-like-to-talk-to-this-older-man.html
In which case, perhaps re-read the answers you got last time? Or did nobody give you the answer you wanted? In which case, you KNOW what you want to do, so do it.
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