Olive paste may exert bioactivity due to its richness in bioactive components, such as oleic acid and polyphenols. The present interventional human study investigated if the fortification of cookies with olive paste and herbs may affect postprandial lipemia, oxidative stress, and other biomarkers in healthy volunteers. In a cross-over design, 10 healthy volunteers aged 20–30 years, consumed a meal, rich in fat and carbohydrates (50 g cookies). After a washout week, the same volunteers consumed the same cookie meal, enhanced with 20% olive paste. Blood sampling was performed before, 0.5 h, 1.5 h, and 3 h after eating. Total plasma antioxidant capacity according to FRAP, ABTS, and resistance to copper-induced plasma oxidation, serum lipids, glucose, uric acid, and antithrombotic activity in platelet-rich plasma were determined at each timepoint. There was a significant decrease in triglycerides’ concentration in the last 1.5 h in the intervention compared to the control group (p < 0.05). A tendency for a decrease in glucose levels and an increase in the plasma antioxidant capacity was observed 0.5 h and 1.5 h, respectively, in the intervention compared to the control group. The remaining biomarkers did not show statistically significant differences (p > 0.05). More clinical and epidemiological studies in a larger sample are necessary in order to draw safer conclusions regarding the effect of olive paste on metabolic biomarkers, with the aim to enhance the industrial production of innovative functional cookies with possible bioactivity.