This qualitative multiple case study aimed to unveil the lived experiences, and coping strategies of five middle-aged learners from local colleges in Davao del Norte: single-male, married working-male, single-parent female, married working-female, and married full-time student female, which were chosen through maximum variation sampling. Their experiences and coping strategies were examined using in-depth Interviews. Data triangulation was done by interviewing each case’s family members, colleagues, and friends. Thematic analysis resulted six emergent themes on the experiences: linguistic barriers in communication, strong resolve towards linguistic resilience and growth, aspiration for personal and professional growth, varied ESL engagements, multifaceted support network, and learning challenges. The emergent themes for coping mechanism included reliance on reputable sources, self-directed learning strategies, social support system, optimal use of technology, English language immersion, and stress management technique. The five cases were generally similar in their experiences and challenges, but three cases manifested variation in linguistic barriers, and two for strong resolves towards linguistic resilience and growth. As for coping strategies, five cases adopted varied approaches in time management and prioritization, and three cases differ on self-directed strategies. All cases shared the same coping schemes from the rest of the strategies in dealing language learning challenges.