The same ol' bland conversation can get boring after awhile. Relationships should be entertaining and that usually starts with the conversation. Next time you're out somewhere, or at home and just looking to liven up the mood a bit, try asking your boyfriend a funny question, or giving him an entertaining statement. Be careful though; although some might leave him loving you more, others might have him looking for a new girlfriend.
For most boyfriends, there will be no phrases that will gain attention like the phrase "I'm pregnant." He's unlikely to be thrilled at the statement and it'll be doubtful you'll hear a laugh, but at least you can have a good chuckle out of it. Remember to tell him relatively quickly that you're just joking, or it could lead into an unintentional fight. Once you explain yourself, he should be so thrilled at the prospect that you were joking that the rest of the day should be a breeze.
"What's the Smartest Thing You've Ever Done?"
This is really a trick question, which is what makes it fun to ask. "What's the smartest thing you've ever done" should result in an immediate answer of "find you," "snatch you up," or some similar phrase with the same meaning. If he answers incorrectly by saying something else, then you can immediately correct him and scold him for his incorrect answer. You can test him again in a few weeks to see if he learnt his lesson.
"What was Your Worst Dating Experience?"
Asking or telling your worst dating experience can be fun with a boyfriend. It gives you an opportunity to both have a few laughs and at the very least will make you feel ecstatic about your current relationship --- unless of course his worst dating experience featured you.
"Do You Think I'm Fat?"
Probably the most confusing question for a boyfriend to answer is the dreaded "fat" question. Although he'll almost always answer "no," you can still toy with him, continuing the conversation just to watch him stumble around this difficult territory. Tell him to just tell you the truth and that it's OK if he thinks that. Of course, this type of fun can easily backfire if you end up getting an answer that doesn't suit you well.