"(I) aJessica doesn't actually need a different font and she really doesn't need to make the words bold. And she's right, trying to enlarge the front by dragging the corner will only make it way too big. The trick is using the offset tool. Let's take a look.
For this example, I'm going to use a very thin script font called Edwardian Script ITC. I start by typing out my words in Silhouette Studio using the text tool, just like I normally would for text. Even in font size 72, the font is very thin in many areas. If I tried cutting it like this on vinyl or even paper it would likely tear.
If I zoom in a bit you can really see how thin the font is...
Even just slightly thickening the letters will help when it's cut.
To do that, highlight all of the text (whether it's a single word or a sentence) and group it. (Highlight > Right Click > Group) This will help us out later. While the text is still highlight clicked the 'Open the Offset Style Window.' Click 'Offset'. Now breathe and do not panic when your font looks like this...
We obviously need to make a few adjustments. The default offset is .25" which is way too large for this font. We want to really bring the offset in, but before you do zoom in so you can really see what you're doing. Now you can adjust the offset distance. I found around .025 or .02 worked well with this example. The offset distance that works on your text, though, will all depend on how large the original font size is. You want it to be pretty tight so the detail in the font isn't lost and so the letters don't start blending together. If you make the offset distance too large, you may lose 'middle' areas of letters like the 'f' and in the top of the 'T'.
You can also change if you want the offset to have rounded or straight corners. I changed mine from the default of rounded corners to straight since the font has straight angles in areas like around the cross of the "t".
Here's how my text looked after the offset distance and corner adjustments. If you look closely, you can see there is a slight outline around the original text...that's the offset I just created.
Once the offset is how you like it, you can pull the original text (top) away and delete it. Just highlight it (this is why you grouped it) and drag it away from the offset. You'll be left with just the offset (below) as your cut. Can you see how the offset on the bottom would be much more Silhouette friendly?
Here's another example of using an offset on text to make it just slightly easier to cut - this one is on a sans serif font.