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How can I develop this friendship into a relationship without scaring him off?

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Question - (21 February 2009) 11 Answers - (Newest, 22 February 2009)
A female United States age 41-50, anonymous writes:

I met a boy through a dinner gathering twice. Since that second meeting, we've been chatting almost everyday several times a day, occasional texts, comments actively on my facebook wall - mostly his initiation. Intuitively, I thought he liked me and was interested. I'm 33, he's 22. When I first found out, I was shocked because he comes across more mature and looks like he's in his mid-upper 20s. He reluctantly told me his age b/c, 'it changes things'. He knew I was older, but he thought I was 24 (nice - ha!). I continued to chat with him b/c it was simply enjoyable, we clicked and yes, I think he's cute! He's also single and not dating anyone.

While we were chatting, it just confused me why he wasn't asking to hang out offline, one on one? If we get along so great online, why not take it offline since we're only a town away? I threw out a suggestion once, but that was it - no follow through. I thought it was probably because we were both traveling on and off during the time and also had bad weather, ie snow storms. I became patient.

A little while ago, he told me he was relocating (7 hour drive) b/c of a new job opportunity. Just a week after this news, he dropped the bomb on me and told me he already relocated and started working at the new job. During that same , we were still chatting on and off and he didn't mention anything about actually moving. I sarcastically said, thanks for saying goodbye! He laughed it off and said he's 'shady and sketchy' like that. He said he doesn't typically say goodbyes and said he can still come to the city (where I am), and can still attend upcoming dinner functions (where we met). He made it sound like, there would be no major difference.

I pulled back from him as a result of this. I would think that before he moved, he would attempt to get together with me? Now, I keep the chats short, and on the surface, ie not talking about my personal life, block IMs every now and then. He's noticed and asked why I'm not telling him what's up, what's new and that I'm avoiding. I still dodge his questions because I feel like I'm playing *his* game by being selectively evasive.

The truth is, I was really attracted to him when I met him (albeit just twice) and I was pretty sure he was attracted to me. I liked him more as our 'chat relationship' continued, regardless of age, and it's obvious that he did too. So why is he not taking it offline? Is there a new online-offline dating/relationship trend I'm not aware of? Is he *just not that into me*? Should I do The Rules for Online Dating to test it out? How can I develop this friendship into a relationship without scaring him off?

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A reader, anonymous, writes (22 February 2009):

Believe me, I have thought about writing a book! If he is pursuing this, and you are comfortable enough to take the risk, then go for it. If nothing else, it is a great ego boost! And who knows where it will lead!

Good Luck, and Enjoy!

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A reader, anonymous, writes (22 February 2009):

This is verified as being by the original poster of the question

britt, i've heard that too! since i've been pulling back, i feel like he's been trying to get my attention, albeit online. ie, initiating ims, sharing links related to my interest, repeatedly asking what's new on my end. i first met him in nov, second time in jan. chatting/text/fb ever since.

you're so right about the feelings! you would think at my age i'd have written books on this by now, but no.

thanks again for your help. i guess only time will tell the rest.

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A reader, anonymous, writes (22 February 2009):

Oh, okay, so you actually do know him. Well, you know younger men are sometimes intimidated by older women. I recall someone on this site (male) writing in telling us he was attracted to an older woman, and wanted to know what older women liked, how he should treat her, and how he should act in general...like we are any different than women in thier 20s! I told him no matter what age we are, when we are in love with (or attracted to) someone, we feel like teenagers! Don't you agree?

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A reader, anonymous, writes (22 February 2009):

This is verified as being by the original poster of the question

it started offline...i met him twice at group dinner get-togethers. it was after the second meeting, the online friendship began.

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A reader, anonymous, writes (22 February 2009):

Yeah, especially when It starts online, and then goes offline! I know what you mean. Well, good luck with whatever happens. I hope you find happiness!

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A reader, anonymous, writes (22 February 2009):

This is verified as being by the original poster of the question

britt, thanks so much for your reply! i think me using the term 'boy' might be misleading here. i don't use it literally, it's just a casual term i use for guys every now and then. sorry if it caused some confusion.

my previous ex was 5 years younger than me, and i always thought that was the youngest i could go. it's reassuring hearing your example, as i'm sure there are countless others.

since it's so difficult for me to meet guys that i am attracted to and also connect with, my hopes was to get to know him better in hopes for a romantic connection. i thought it may have been mutual with his numerous initiated communications. to my disappointment, he just never asked to meet/hang out offline one on one. he seems content with the online friendship, whereas i prefer more of an offline connection.

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A reader, anonymous, writes (22 February 2009):

First off, If you are thinking of him as a "boy" rather than a "man" I think you should back off. Although young, a 22 year old is a man!

At the age of 36, I was engaged to a man of 24. I actually was the one to call it off, because he was just too serious for me! I too looked younger than my age back then.

Age to me, is just a number. My ex was 7 years younger than me. My current boyfriend is 4 years older than me. It's not about age, it's about a connection...physically, emotionally, and spiritually (I am not talking religion here) There are some considerations to think about...intentions? What are Your intentions, what are his? If you just want to hang out and see what happens that's fine, but it may not go further than that.

Good Luck

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A reader, anonymous, writes (21 February 2009):

This is verified as being by the original poster of the question

no offense taken...i used to say that at your age :)

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A male reader, anonymous, writes (21 February 2009):

The original poster makes strong points. The age gap is probably too much for him. I'm 24 and would never in a million years date a girl that much older (No offence intended).

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A reader, anonymous, writes (21 February 2009):

This is verified as being by the original poster of the question

Butterflykisses, thanks - I appreciate your reply and honesty! Just to clarify,

* he didn't want to tell me his age b/c he was afraid I would turn away, or that I would treat him differently.

* i'm pretty sure he relocated.

I agree, that if he wanted to have hung out, even just as friends, he would have and not rely on that dinner event we both go to.

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A female reader, ButterflyKisses United States +, writes (21 February 2009):

Guys are actually pretty simple. If he wanted an offline relationship with you - he would pursue it. My advice is to hold yourself to a higher standard and move on. I respect his honesty. He said he was, "shady and sketchy" like that, and while I assume he said that as a joke, I think there was more truth behind that. The evidence is laced throughout your post.

You've done everything to let him know you're interested (i.e. suggesting that you met up offline) and he's done everything to let you know he's not interested (i.e. blowing off your suggestion to meet up, stating the age "changes everything," conveniently relocating without telling you, etc.) My guess is that he did NOT relocate, but can now use this as an excuse NOT to meet up, or commit to any type of relationship.

I know this is not want you wanted to hear, and it's not fair. I'm sorry you're dealing with this.

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