Trunk Club uses personal stylists to send your man curated clothing and accessories each month, which he can accept or reject.
It looks like the stylists are mostly young, cute women, so he'll probably be really into it.
Whiskey Stones: Even though there won't be a President Hillary around to personally cut off all our balls and literally end men as a gender (there really are people who thought this), most men are still fucking sheep and look to fictional characters like Ron Swanson for guidance in "how to be a man." To that end, these whiskey stones are the perfect analog for modern manhood: superficially authentic, but ineffectual (they will not actually keep his drink cold).
As a bonus, if he's a little too excited by these, you know you're dealing with one of "those" guys. Birth Control: Not for him, obviously, but for you (for him). Condoms are the devil, even if they do protect against most STDs.
Horology is one of those things that a small subset of very annoying people get way too into (hence the term horology), but you don't need to go hunting for a vintage Patek Philippe that costs more than your literal worth as a human being.
Tile Mate: If there's one thing I know to be true of my gender, it's that we lose shit CONSTANTLY—not least of all because it's so much easier to whine "honeyyyyy, have you seen my keys?
" But you're probably not on a pet name level yet, and you certainly don't live with him. It's a little gadget that attaches to whatever he wants, so when he loses it, his phone can help him find it.
No one's saying you need to buy a sex swing, just change it up a little bit. Post some anonymous n00dz to r/gonewild and have some hot sex to the thought of a bunch of Reddit nerds fapping and diddling themselves to your naked splendor.
Break out a vibe and do some diddling while he watches. Anything to convince him that his best days aren't behind him, really.
You've been going for a while now, so I think it's safe to say you've got a good thing going. An EDC Kit: Short for "everyday carry," these kits aren't unlike the whiskey stones in that they're a largely useless prop of performative masculinity—"real men are always prepared," etc.