You might try going to an organization called Toastmasters. They are an organization dedicated to teaching (and inspiring) leadership, but they can also help you to become more confident and their specialty is public speaking (not that you need to become a public speaker) But I have heard good things about this organization being able to help shy people and people who have confidence problems. There are branches all over the country.
Let your boyfriend know that you are really trying to overcome this problem. Let him know that you need to go slow and steady and come up with some type of phrase or word that you can use to let him know if he’s pushing you too hard, but then decide today, right here and now, that you are going to let your boyfriend help you.
You can get better at learning how to express yourself verbally by playing question and answer games. I’ll give you some examples, but then come up with as many as you can, and ask your boyfriend to come up with some too. Write them all out and then every day you guys can ask and answer questions, starting with easy ones (like what flavor of ice cream you like best) to intermediate ones like (how come you always choose chicken nuggets at the restaurant and not anything else) to more difficult ones like (how did your parent’s divorce effect you). You should play this question and answer game every day, starting today and maybe just ask and answer a few questions for the first few days until you get more comfortable with it. But NEVER give a one word answer or just a yes or no. You need to really think about the answer and then give some sort of supporting statement and add some other information that might be related to the question.
Here’s an example:
Q: What is your favorite ice cream?
A: I like strawberry, but when I was little my brother talked me into tasting this really sweet dark chocolate ice cream with marshmallows, Rocky Road. I liked it ok, but the nuts and things were kind of weird. My Dad always preferred Ben and Jerry’s Chunky Monkey and my Mom liked Mint Chip. I really enjoy going to the ice cream parlor and I remember a place from my youth called Farrell’s. They don’t have any Farrell’s anywhere anymore, but I loved the fact that they had this huge candy store within the ice cream parlor. My folks always let me and my brother pick out one type of candy on the way out. I always got these things called rock candy, that looked like little ice cubes on a stick. They were pure sugar and the thought of them, now, kind of makes me sick. They aslo had candy cigarettes, which I can’t even believe that they allowed that kind of thing. I wonder if anyone still makes those? My brother’s favorite was Sugar Daddys, but I didn’t like them as much because they always stuck to my teeth. My parents took me and about 10 other kids from my school to Farrell’s for my 6th grade graduation. You should see the awful photos, it was hilarious!
See how the answer was relatively simple, but there was a whole lot of other related information that could be added. That’s what really makes for a conversation rather than just small talk or a plain and simple answer.
So here’s a list of potential questions:
Who was your favorite teacher in grade school? What did you like about him or her?
Did you ever go to Disneyland or other theme park when you were a kid? What was it like? Describe it in detail sights/sounds/visuals/scents etc.
If you were going to plan a dream vacation, where would you like to go and what kinds of things would you like to do/see/eat/photograph/experience on that trip?
When you think about love, what does it mean to you?
What were your parents like when you were growing up? Have they changed now that you are an adult?
Did you ever have any kind of traumatic situations happen to you when you were a kid? How did you deal with it?
What kinds of movies or books do you like and why?
You should scroll through the Fluther questions and use some of those too! And you can and should play this game with your family and other friends too. And remember that real conversations are always 2 way streets. When you are talking and answering the questions, ask your partner questions about the same subject or about other things that pop into your mind while you are talking, go back and forth between talking and asking questions and listening. Good luck and please get back to us and let us know how you are progressing.