Hello BawlBuster703,
Thanks for reaching Microsoft Community and posting your concern here.
The earbuds are typically a tighter fit, so you ideally won't have to push them back in constantly, and the over-the-ear variety make the earbud fit a non-issue. Try to place the earbud in your ear with the tip pointing slightly downward, and then gently twist it backward until it feels comfortable and secure. It should sit in your ear without sealing inside it and being forced. This lets you get the sound you want while still hearing ambient sound around you. See Find your fit for Surface Earbuds to find out more.
Hope this helps.
StevenK