JSFiddle - React, Tailwind, and code Playground

HTML

<ul class="grid__row grid__row--sm">
    <li>1 small</li>
    <li>1 wide wide wide wide wide wide</li>
</ul>
<ul class="grid__row grid__row--sm">
    <li>2 medium medium</li>
    <li>2 small</li>
</ul>
<ul class="grid__row grid__row--md">
    <li>3 small</li>
    <li>3 wide wide wide wide wide wide</li>
    <li>3 medium medium</li>
</ul>

CSS

.grid__row {
    margin: auto;
    padding: 0;
    list-style-type: none;
    display: flex;
    flex-direction: column;
}
.grid__row li {
    background: green;
    color: white;
    margin: 1px;
    padding: 15px;
    display:flex;
    flex: 1;
}
@media (min-width: 480px) {
    .grid__row--sm {
        flex-direction: row;
    }
}
@media (min-width: 768px) {
    .grid__row--md {
        flex-direction: row;
    }
}