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How to date an awkward person. Any advice?

Tagged as: Dating, Teenage<< Previous question   Next question >>
Question - (22 October 2015) 2 Answers - (Newest, 23 October 2015)
A female United States age 22-25, anonymous writes:

Hi, So I'm talking to a guy who is very sweet and we both really like each other. However, he's very awkward. Even with his close friends he's still sort of reserved. He laughs and talks with them but there's still shyness with friends he's completely comfortable with and has known for years. It's pretty much his personality.

I, on the other hand, am a talkative person once I get to know someone but even then I'm not a great conversation starter. I can keep a conversation going and have good and fun ones, I just can't start them.

I don't really know what to do because I've expressed how I have felt and he has expressed that he wants to talk as well but he is also aware of his awkward personality. We text well and can talk there for hours but he's just not very sociable in person. He also has expressed that he is intimidated by groups of people. Especially my friends.

For example, he is in my history class. Three of my friends sit directly in front of or next to him so before and at the end of class I am near him. He however doesn't say anything to me and hardly acknowledges me, however I can tell he is listening and is often times entertained by what I say with my friends. I told him we should talk in history more since that's our only class and he said he wants to but the amount of people in the class gives him a pressured feeling.

I really like him and we both have expressed the interest in dating. We are basically at the point where we're both just waiting for him to work up the courage to ask me to be his girlfriend. I told him to take his time and ask when he's ready, and I am in no rush. I just want to solve or at least become educated about how to address the problem at hand. I don't want to bring it up again or too often because I'm afraid it will get annoying, and this could lead to the end of our talking phase, and prevent or delay our relationship, so I don't want that.

Is there any way to get used to this or solve the problem at hand? If there is a solution, how do I bring it up in a manner that keeps him from losing interest?

Thanks for the help,

-S

View related questions: shy, text

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A male reader, Denizen United Kingdom +, writes (23 October 2015):

Denizen agony auntWhen I was your age it used to work by using a go between. A friend would ask one of his friends if he was interested. If he was the next thing would be a not exchanged. Then you might meet up on a Saturday or perhaps after school somewhere for a coffee.

From that it would move on to a disco or cinema. Meeting up for walks is nice to because you can talk and maybe kiss. Walking together allows for hand holding and getting a bit closer.

The thing about girls is that they are far more gnarly than boys think they are. So, often boys, if they are shy, treat girls like they will shatter. or be repulsed by them.

Grab his hand. Plant a kiss on his cheek. Let him know he is not going to be turned away or humiliated. Boys fear that the most.

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A female reader, anonymous, writes (23 October 2015):

Hi there :)

It is quite normal for a guy to feel shy at this age. tbh, sometimes guys don't wanna ask their love interest to be their gf because they are afraid of losing them. I have experienced this. It may some time before he asks you to be his gf. For me, I waited 6 months... Maybe you could text him and chat about this. Dont be mad with him about this. It is more common than you think. But maybe you could ask him about what are you guys considered... do it subtle way... i hope this helps..

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