I've been using sippy cups on my kids for many years now, and while there are so many nice fun ones to choose from, I have had the best luck overall by far with the playtex ones. They are sorta boring, don't come in cool characters or anything exciting, but not only are they the most spillproof, but they also hold up the best. I had used the old-fashioned playtex bottles, and the sippy cup is similar in feel, so her natural instinct was to put it to her mouth and suck, as with the bottle. Has your boy used a bottle before or has he always been breastfed? If he's always been breastfed, then it'll just take some getting used to but I'd say to keep the breast as far away as possible when trying to use the sippy cup, in fact maybe have Dad try, and put breastmilk in there.... Oh, and I just remembered one other thing. When my daughter was about that age, I couldn't get her to eat hardly anything. I always had to resort back to carrots and sweet potatoes. By the time she was about two, I was fed up with it, because she'd incorporated chicken nuggets into the diet, but very little else. So I went out and bought a bunch of books. Basically what it came down to, was that these babies are WAY smarter than we realize! They have already got us all figured out! They KNOW that if they turn down the new food, we're not going to let them starve, so we're going to try a time or two more then give up and give them what they want. And as long as they know that, they'll use it. So I took it to the test, and incorporated a new plan. Before, I'd pull ten different things out of the cabinet before I could find what she'd want. How about chicken and mashed potatoes? no... How about.... and no would be the answer to all of them. When she'd finally say yes to, say, mac & cheese, i'd pull it out and make it, and she'd take a bite and change her mind. Not hungry anymore. It was like some sort of performance - let's see how long I can make mom dance - and it was so frustrating! This is when I decided to make a change. I started fixing dinner for myself, with enough extra for her, and I'd put it in a little tupperware (so if she didn't eat it i'd eat it as a snack the next day). I started out with somewhat kid-friendly foods, like meatloaf, peas & mashed potatoes. I'd sit down to eat, and make her sit with me. If she didn't want to eat it that was fine, but she had to sit there w/o tv or anything, and would get no dessert or any other food that night. She didn't have dinner for three nights in a row. I was pretty frantic, and was convinced DEFACS was going to come and get me. In fact I called them to let them know what I was doing just to be sure... and they did say that was ok. Finally she started to SORTA eat what I was eating, but wouldn't eat much. But within a few weeks, she was sitting down with me eating Grilled Fish and asparagus one night, and a greek salad the next! (and she's learned to like it all!) I am SO proud of both her and me now, because I can take her anywhere and she eats everything. She is a cultured little girl. Yes, she still loves Chicken Nuggets more than any other food on the planet, but now they are just used as a treat - like when many moms might allow their kids candy, her big treat is chicken nuggets. If we're with other kids, and they're havign candy, I'll let her choose betwen the candy or I'll tell her I'll get her nuggets instead and she'll usually hodl out for the nuggets :o) I had explained to her a while back that they make you fat if you eat them too often, and that all fast food restaurants do that. And that if you're fat, you can't run as fast, and can't play as much. So she was ok without having them too often. But one day we were at Wendys, and I'd gotten her chicken nuggets, a yogurt and mandarin oranges, and this lady walks past us with a supersize value meal of some sort and my daughters eyes popped wide and she said (rather loudly) "Oh my gosh she is going to be SOOO fat!" I was humiliated! So now we go through the drive-thru ;o) (I've also had the talk about "Remember what Thumper says?" (He says that if you don't have something nice to say, don't say anything at all.