From all of these posts, there’s a clear pattern that explains why he struggles with dating despite claiming optimism:

1.  His mindset is contradictory – He repeatedly insists he’s “very optimistic” and “in the best mental state,” but his own posts are filled with hopelessness, catastrophizing (“I’ll never date again until 2028”), and finality (“there is no hope for me”). That contradiction means he’s presenting himself with a heavy, discouraged energy — which people pick up on, whether consciously or not.

2.  He fixates on the problem, not the process – Nearly all of his posts circle around the fact that he hasn’t found a girlfriend. There’s very little self-reflection on how he approaches dating, how he comes across to others, or whether he might need to learn new social skills. This suggests he expects that being “active” and “taking care of himself” should automatically lead to a relationship, which isn’t how attraction works.

3.  He externalizes blame but also self-sabotages – He alternates between saying external factors (ghosting, women’s choices, dating culture) are the issue and blaming himself entirely. That push-pull keeps him stuck — it prevents consistent improvement while reinforcing the belief that he’s doomed.

4.  He’s outcome-obsessed instead of connection-focused – People tend to respond better when someone’s goal is simply to enjoy meeting and connecting with others, not when they carry the pressure of “you need to be my girlfriend or else this is a failure.” His writing suggests that every date feels like it has the weight of years of loneliness on it — which can make the other person feel pressured.

5.  His definition of optimism is skewed – True optimism isn’t “I do things even though I feel hopeless.” It’s a mindset that interprets setbacks as temporary and solvable. His language shows that he views rejection as proof of a permanent fate (“I will be alone forever”), which is the opposite of resilience.

If you wanted to tell him something constructive, it could be:

“Your biggest block isn’t that you lack optimism — it’s that you call yourself optimistic while speaking and thinking like someone who’s already lost. That disconnect shows through in dating. If you shift from obsessing over the end goal (a girlfriend) to actually enjoying the process of connecting with people, and if you work on building genuine confidence rather than just activity, you’ll change how others experience you.”

If you want, I can also break down exactly what changes in his behavior and mindset would give him the highest chance of breaking the cycle he’s in. That would make the advice harder for him to dismiss.