This retrospective study surveyed decision-making and challenges among 78 gay cisgender male couples utilizing in-vitro fertilization (IVF) and a gestational carrier. While most couples (67.1%) found the decision to actively pursue fertility treatment 'not difficult', 32.9% felt that it was 'somewhat difficult' or 'very or extremely difficult'. Almost 30% of couples had not undertaken financial planning for treatment, which introduced delays of N 2 years for 25.3% of participants. Conceiving twins was 'important to very important' in 52.3% of couples, and 84.2% of couples chose to transfer two embryos to 'increase the odds' or reach an ideal family size in a single attempt despite increased complications with multiple pregnancies. Paternal leave was granted for one partner in 47.3% of couples, and for both partners in 43.2% of couples. One-third of couples reported experiencing discrimination, prompting a partner to seek employment, and 38% changed jobs or careers. For 80.3% of couples, the estimated cost exceeded US$100,000. Couples where one partner was aged N 50 years were significantly more likely to find the decision to actively pursue fertility treatment 'very or extremely difficult' (28.6%), and less likely to agree on becoming parents (64.3%). Gay male couples undergoing assisted reproduction face challenges regarding decision-making, lack of infertility benefits and discrimination, which appear to be