Introduction. Failure to find information is common. An exploratory analysis of cases when family members or friends were asked for information can provide better understanding of when, how and why interpersonal information seeking within a close network of individuals fails. Method. A sample of utterances (in form of "I asked my mum, but") was harvested from the Web using LexiURL Searcher software. Analysis. The material (327 utterances) was analysed with content analysis and categorised using the constant comparative method. Results. People utter on the Web different types of, mostly fact-related, questions they have asked earlier of their family members and friends. Multiple factors were found to affect interpersonal information seeking including a major barrier, bashfulness, which has not been discussed earlier in the literature. Conclusions. Success in asking questions of family and friends is a broad issue of mastering information content, social environment and other contexts of information seeking rather than a technical ability. (Contains 3 tables.)