Background There is growing interest in the use of information communication technologies to treat obesity. An intervention delivered by smartphone could be a convenient, potentially cost-effective, and wide-reaching weight management strategy. Although there have been studies of texting-based interventions and smartphone applications (apps) used as adjuncts to other treatments, there are currently no randomized controlled trials (RCT) of a stand-alone smartphone application for weight loss that focuses primarily on self-monitoring of diet and physical activity. Objective The aim of this pilot study was to collect acceptability and feasibility outcomes of a self-monitoring weight management intervention delivered by a smartphone app, compared to a website and paper diary. Methods A sample of 128 overweight volunteers were randomized to receive a weight management intervention delivered by smartphone app, website, or paper diary. The smartphone app intervention, My Meal Mate (MMM), was developed by the research team using an evidence-based behavioral approach. The app incorporates goal setting, self-monitoring of diet and activity, and feedback via weekly text message. The website group used an existing commercially available slimming website from a company called Weight Loss Resources who also provided the paper diaries. The comparator groups delivered a similar self-monitoring intervention to the app, but by different modes of delivery. Participants were recruited by email, intranet, newsletters, and posters from large local employers. Trial duration was 6 months. The intervention and comparator groups were self-directed with no ongoing human input from the research team. The only face-to-face components were at baseline enrollment and brief follow-up sessions at 6 weeks and 6 months to take anthropometric measures and administer questionnaires. Results Trial retention was 40/43 (93%) in the smartphone group, 19/42 (55%) in the website group, and 20/43 (53%) in the diary group at 6 months. Adherence was statistically significantly higher in the smartphone group with a mean of 92 days (SD 67) of dietary recording compared with 35 days (SD 44) in the website group and 29 days (SD 39) in the diary group (P<.001). Self-monitoring declined over time in all groups. In an intention-to-treat analysis using baseline observation carried forward for missing data, mean weight change at 6 months was -4.6 kg (95% CI –6.2 to –3.0) in the smartphone app group, –2.9 kg (95% CI –4.7 to –1.1) in the diary group, and –1.3 kg (95% CI –2.7 to 0.1) in the website group. BMI change at 6 months was –1.6 kg/m2 (95% CI –2.2 to –1.1) in the smartphone group, –1.0 kg/m2 (95% CI –1.6 to –0.4) in the diary group, and –0.5 kg/m2 (95% CI –0.9 to 0.0) in the website group. Change in body fat was –1.3% (95% CI –1.7 to –0.8) in the smartphone group, –0.9% (95% CI –1.5 to –0.4) in the diary group, and –0.5% (95% CI –0.9 to 0.0) in the website group. Conclusions The MMM app is an acceptable and feasible weight loss intervention and a full RCT of this approach is warranted. Trial Registration ClinicalTrials.gov NCT01744535; http://clinicaltrials.gov/ct2/show/NCT01744535 (Archived by WebCite at http://www.webcitation.org/6FEtc3PVB)