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Advice on making a move on my shy boyfriend?

Tagged as: Dating, Sex, Trust issues<< Previous question   Next question >>
Question - (7 October 2009) 4 Answers - (Newest, 9 October 2009)
A female United States age 30-35, anonymous writes:

So my boyfriend and I have been dating for about 5 months now. We work togther at least 2 times a week, and try to see eachother on our days off together. Our days off usually mean hanging out at his apartment with his roomates and me staying the night.

When we go to bed, we crawl into his bed togther, kiss goodnight, and go sleep. The first couple of times this happened I thought it was a little weird that it was just "kay 'night". I mean what 22 year old guy with a girl in his bed doesn't try anything? The thing is, I've grown to learn that he's impossibly shy. He's sarcastic and a smart ass, so I always think he has more confidence than he does, but he's just that shy.

The bad part is that I'm shy too, ontop of being insecure about pretty much everything about me. I just go along with it and sleep, thus discouraging him.

I was at his place a couple of days ago, making it at least my fifth time sleeping over, and I could see that he was trying to make a move on me but it didn't really follow through. Instead of trying something back at him, I didn't, and I think that's the problem.

So I guess my question is how could I start doing things in bed with him to show that I'm interested?

Within his and my insecurities of course. For example, I had a friend tell me to just stick my hand down his pants, or wear just my underwear to bed. First off I have nowhere near the confidence to do that, and secondly, I have no idea if he would be comfortable with that at all.

So I'm asking for a modest, innocent way to just give him something that says "it's ok, I'm willing for whatever you want to do".

I'm not going at this for sex as a goal either, just something to step up the relationship a notch for two people too shy to do it on their own.

View related questions: confidence, insecure, move on, shy, underwear

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A reader, anonymous, writes (9 October 2009):

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

We do spoon togther, mostly because I love to cuddle, but we do spoon and are generally close in bed together.

We have also started french kissing instead of just a peck goodnight, but once I think he's going to take it somewhere, he just says goodnight. That's why I think he's just waiting for me to do something back.

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A male reader, hany Egypt +, writes (9 October 2009):

hany agony auntI'm just can't imagine that tow sleeps together in one bed and do nothing

here it is some ideas, I'm good at advice

it will start by change the way of kissing from goodnight kiss to something another like french kiss, i think it's will give you and him some courage

try to seduce him a little, not by sleeping by your underwear but i think something like see-through pajamas will do the trick

try to see together some romantic R or PG13-rating movies in Saturday nights, This will ignite the feelings

hopes this will help, and sorry for my English

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A male reader, anonymous, writes (8 October 2009):

Yeah, i'm kinda like that too. I guess it's out of respect for the girl. I don't want her to think i'm in it for the sex.

Don't stick your hand down his pants. Just think of something clever and funny to say.

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A female reader, HereAreMyTwoCents United States +, writes (8 October 2009):

HereAreMyTwoCents agony auntWell, if you're not having sex, and you want to step it up but not all the way to sex, I think that the next logical step is sleeping together in a spooning position to get comfortable to each other's bodies together, and to heighten desire by creating the constant physical closeness during the night. So next time you're in bed and kiss goodnight, instead of settling down on your own pillow, spoon up to or into him. And while you're there, you can start exploring his body with your hands. Hope that helps.

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