HowAboutwe

High-Level Overview

HowAboutWe is a digital lifestyle company founded in 2010 that built online platforms for dating singles and curating experiences for couples, emphasizing real-world dates over endless online chatting.[1][2][3] It served millennials seeking authentic connections by letting users post and match on date ideas, while expanding to couples' tools like messaging apps and activity recommendations; the platform grew to 2.3 million users, $22.3 million in funding, and operations in multiple U.S. cities and 30 countries before its 2014 acquisition by IAC (owner of Match.com and Tinder).[1][3][5] Post-acquisition, it relaunched with features like "Tonight" for instant dates and "Connections" for daily matches, solving the problem of swipe fatigue by prioritizing offline interactions.[3]

Origin Story

HowAboutWe emerged from founders Aaron Schildkraut, David Ackerman, and Brian Schechter's frustration with inauthentic online dating—endless profile browsing and poking that felt banal for millennials.[1] The idea crystallized during a reflective period in Boston at Schechter's family home: "Why isn’t there a dating app that’s actually about dates?" They launched in New York in early 2010 as "the first offline dating site," focusing on users proposing real-world date ideas to foster quicker, genuine meetings.[1][3][5] Early traction included rapid user growth to 1.7 million for singles and 500,000 for couples, plus expansions like international iOS apps in 15 languages and acquisitions of media properties (Nerve, Swimmingly, Famously).[1][5] A pivotal moment came in July 2014 with IAC acquisition, enabling a full relaunch on its fifth anniversary with refined features.[3]

Core Differentiators

• Date-Centric Matching: Unlike swipe-heavy apps, users post specific date ideas (e.g., "dinner at X") to match and meet offline quickly, reducing misleading chats and emphasizing shared interests over photos.[1][3][5][7]
• Real-World Focus: Features like "Tonight" for instant same-night dates, "Connections" (5 daily matches), and "Pool" (Tinder-like browsing) balance immediacy with exploration, pushing interactions beyond screens.[3]
• Couples Ecosystem: Standalone tools like a free iOS messaging app with Photobooth, Halfsie, and Trick filters for shared content, plus curated experiences and discounts in cities like NYC, Seattle, and LA.[2][4][6]
• Media and Lifestyle Expansion: Acquired Nerve (love/culture mag) and launched Date Report, Swimmingly (couples lifehacking), and Famiguously (celebrity/entertainment) for broader engagement.[1]

Role in the Broader Tech Landscape

HowAboutWe rode the early 2010s shift from profile-saturated dating to activity-driven, mobile-first experiences, countering "swipe fatigue" in a market dominated by Tinder and Match.[3][5] Its timing aligned with smartphone ubiquity and on-demand culture (e.g., instant cabs/food), making offline dates a natural evolution—launching internationally free to build critical mass amid rising global mobile dating.[5] Market forces like IAC's consolidation favored it, blending indie innovation with scale; it influenced the ecosystem by proving couples' retention tools and media adjacencies could extend dating apps' lifetime value, paving the way for hybrid social-romance platforms.[1][3]

Quick Take & Future Outlook

Post-IAC acquisition, HowAboutWe likely integrated into Match Group's portfolio, evolving toward AI-enhanced matching and global scalability amid dating app consolidation. Trends like VR dates, privacy-focused messaging, and wellness-for-couples will shape it, potentially amplifying its offline-first DNA in a post-pandemic world craving real connections. Its influence may grow by inspiring "experience-first" features across competitors, redefining dating from endless swipes back to meaningful dates—proving authenticity endures in consumer web.