The combination that works: flirty says "I'm thinking about you," funny says "and I'm fun to think about back." The texts below do both at once - and none of them require a setup, an occasion, or an apology for texting first.
Playful teasing (the reliable one)
Tease about choices and quirks - reply speed, food takes, team loyalty - never insecurities. Teasing reads as flirting only when the affection is unmistakable.
Absurd commitment (funny because it's confident)
Flirty-funny for long distance
Long-distance flirting runs on maintained bits - the daily report, the running scoreboard, the fake bureaucracy. A bit you both keep alive does what proximity normally does.
Goodnight versions
(A whole page of these: flirty good night texts.)
Bad vs. better
Why it works: the first asks for his energy; the second supplies its own. Confidence in text form is mostly just declarative sentences.
Jokes written from YOUR chat with him
Paste the conversation, pick the funny tone - callbacks to his actual takes land harder than anything on a list.
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Playful teasing built on something real works best: "I was going to compliment you today but I don't want it going to your head. Maybe Thursday." It's flirty because it implies attention, funny because of the fake bureaucracy.
Tease about choices and quirks, never insecurities - his 45-minute reply time, his weird food takes, his loyalty to a terrible team. The warmth has to be obvious: teasing is flirting only when it's clearly affectionate.
Lean on shared rituals and absurd planning: "Adding 'make you laugh from another time zone' to my resume" or "Daily report: still funnier than you, miss you anyway." Long distance flirting works when it builds an ongoing bit you both maintain.
Yes - paste your conversation and pick the funny tone. Jokes built from your actual chat history (his takes, your inside jokes) land better than any list, because he can tell they were written for him.