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The Weekend is singing

MAYBE YOU CAN SHOW ME HOW TO LOVE

where "HOW TO LOVE" sounds like /haʊdʌv/.

Do Americans usually pronounce "HOW TO LOVE" /haʊdʌv/?

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How to love in that song sounds closer to [haː ɾə lʌv] (or perhaps [həː ɾə lʌv]). It's certainly not [haʊdʌv].

The reason why the t in to sounds like d is 'flapping' (or 'tapping'). In most American accents, d and t before unstressed vowels are usually pronounced with a flap—[ɾ]—in which the tip of the tongue taps very quickly against the alveolar ridge. So water is pronounced [ˈwɑːɾɚ], better [ˈbɛɾɚ], rider [ˈɹaɪɾɚ] (or [ˈɹʌɪɾɚ] in some accents).

In the phrase how to love, the t comes before an unstressed vowel so it's pronounced as a tap—[ɾ].

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