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HowAboutWe

Dating · New York City, United States · Founded 2009

Date-focused platform for singles and couples MoreLess

HowAboutWe was a multifaceted dating and lifestyle company founded in 2009 by childhood friends Aaron Schildkrout and Brian Schechter, both former educators. The founders' objective was to create a dating platform that emphasized offline interaction over endless online profiles, addressing what they saw as a failure of existing sites to get people on actual dates. The core product, HowAboutWe Dating, allowed users to propose date ideas, connecting individuals based on shared interests in real-world activities.

The company expanded its services beyond singles by launching HowAboutWe for Couples, a subscription-based date planning service that offered curated experiences to help couples maintain their relationships. This division reportedly grew nine times faster than the original dating service in its initial stages. To further broaden its ecosystem and user acquisition channels, HowAboutWe ventured into digital media. This media arm grew through the launch of its own blogs, like The Date Report, and the strategic acquisition of the sex and culture web magazine Nerve.com in January 2014. Following the acquisition, Nerve's dating personals were merged into HowAboutWe's platform.

By July 2014, the dating and media assets of HowAboutWe, including Nerve.com, were acquired by the media and internet conglomerate IAC, which also owns other major dating platforms like Match.com and Tinder. The terms of the deal were not disclosed. The HowAboutWe for Couples business was not part of the acquisition and was intended to remain a separate entity. However, the main HowAboutWe platform was eventually shut down following the acquisition.

Keywords: online dating, offline dating, date ideas, couples date planning, relationship services, subscription box, media acquisition, Nerve.com, IAC acquisition, Aaron Schildkrout, Brian Schechter, dating platform, activity-based dating, churn reduction, customer retention, digital media strategy, lifestyle brand

Talent graph

HowAboutWe's talent

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Team profiled 31 named & role-tagged
Founders Hidden — book a demo/100 quality score
Key operators 2 quality Hidden — book a demo/100
Potential founders Hidden — book a demo likely future founders
Startup mafia Hidden — book a demo alumni-founded startups
Talent movements Hidden — book a demo in · Hidden — book a demo out past 12 months

Source: Dealroom Talent Intelligence.

Investors

7 investors on HowAboutWe's cap table

Sourced from Dealroom's funding history. Investor profile links are shown where available.

Series A 7 investors entered at this stage
RRE Ventures
MHS Capital
ff Venture Capital
LaunchTime
Founder Collective
High Line Venture Partners
Khosla Ventures

Global footprint

Where HowAboutWe has talent and traffic

Workforce by country
1 countries with
team presence
🇺🇸 United States100%
1 country shown

Market sentiment

What the market is saying about HowAboutWe

An AI-synthesized read of the highest-engagement posts about HowAboutWe on X over the past 7 days. We rank by likes & retweets, ignore corporate channels, and surface the themes that broke out from real people.

Reading the room on X — pulling top posts and synthesizing themes…

Source: X recent search ranked by engagement (likes + retweets) · Synthesis by Claude · Cached for 1 hour

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