The Pink House is the only gay guest house in Tel Aviv and is run by a very friendly local who acts as a personal travel resource for his guests. There are four separate apartments available, so the tone of your stay will be far more local than at a traditional hotel. The house is ideally located in Center City and Hilton Beach - the main gay beach - is just a 20-minute walk away. Eat breakfast in your own kitchen before heading out for the day.
Use the public shower at the beach before making your way to lunch. Ashtor was one of the first cafés to open in Tel Aviv, and it's maintained a loyal following among locals who appreciate the stellar coffee and people-watching. Grab an outside table, and keep your eyes open; there are a lot of celebrities who own homes in this neighborhood.
Up next, you'll be joining the crowds of local hipsters flocking to the Cinematheque, which is by far the best place in Tel Aviv to see movies. The building is rather nondescript, but take a moment and you'll see the cool kids streaming in and out with nary a tourist in sight. If you're hungry again after the movie, walk a few blocks west to Orna & Ella, a unique restaurant with a cult-like following. You will probably have to wait for a table but the delicious comfort-food is worth it, particularly the sweet potato pancakes.
When it gets dark, you'll probably have some energy to dance off, so walk 10 minutes to Billie Jean at the corner of Rothschild Boulevard and Herzl Street. This is the kind of bar that feels like a dance club and is a good place to avoid the high prices at more trendy spots. It's not a specifically gay bar but does host LGBT events, so the management and clientele are definitely gay-friendly.
If you want to go even deeper into the local underground scene after midnight, check out The Cat and The Dog. There's usually not a cover, the drinks are cheap and the lights are low, so you can focus on the world-class DJs. Don't expect bottles and table service; this is the kind of place that takes pleasure in a little bit of sleaze and caters to a crowd that would rather feel the music than show off their outfit.