Complex sentence: That apparently got the attention of Mr. Coolidge and later that year, Coolidge and Grace Goodhue went out on a few dates when in 1905, Grace Goodhue left the school after only three years of service to marry Calvin and join him in his political career.
Split into simpler sentences: That apparently got the attention of Coolidge and later that year, he and Grace Goodhue went out on a few dates. In 1905 Grace Goodhue left the school after only three years of service to marry Calvin and join him in his political career.