Yeah similar boat here . This girl in high school had a minor crush on me , and after high school we dated for a year . We ' d known each other for years , interacted and partied with the same people and each other . But every friend I ' ve made since has never been interested . The idea of going up to someone and hoping they like my hobbies or share some interests is daunting . I used to get crushes on my female friends for too easily , mostly because I ' d grown to know and like them over the years . But no relationship has occurred again in the 10 years since . I ' ve become good friends with a lot of girls , but none of them had romantic or sexual feelings for me . Most were in happy relationships before I met . It ' s hard to make friends now that I ' m in my thirties , and I find it more and more difficult to enter the dating game again .