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The first playthrough is likely to end with you being alone. If you turn on easy mode and pursue one of the four guys more seriously, you'll likely have better luck in subsequent plays.

But the point of the game isn't dating someone as much as developing your friendships and growing more comfortable with your sexuality, so hopefully you found it enjoyable anyway.

Thank you very much for taking time to reply to all of my comments. Its very enjoyable and I've successfully gotten Jake's ending. Nice game.