Q2 2023 Shareholder Letter

Exhibit 99.2

July 27, 2023

Fellow Shareholders:

Second quarter AEBITDA of $27 million was well ahead of our forecast, posting a decline of only 7% YoY despite the challenging revenue environment across all three business segments. Healthy margins in our Insurance and Consumer segments, along with faster realization of previously announced savings drove the upside. Our ongoing expense discipline and improvements in operating efficiency generated a 15% AEBITDA margin in the quarter, up four points from the year ago period.

Most of the end markets we serve remain depressed due to higher interest rates and the knock-on effects from persistently high inflation. However, we know these headwinds will eventually abate and are encouraged by the declining pace of inflation and indications the Fed is near the end of its tightening campaign. Our focus continues to be on helping our partners through this difficult economic period by providing high quality loan and insurance applicants, and helping our customers save time and money on financial products through an evolving consumer experience. We have consolidated leadership at the company, and have focused our teams on work that will bolster financial results to ensure LendingTree is solidly positioned for growth once healthy demand from our lender and insurance partners returns.

We are thrilled to share that Scott Peyree, our longtime President of Insurance, has also assumed leadership of the Home and Consumer segments as the COO and President of Marketplace. Scott is a proven best-in-class operator in the performance marketing industry who co-founded QuoteWizard and has consistently driven its profitable growth following our acquisition in 2018. Scott helped his team expertly navigate the ongoing decline in marketing spend at our insurance partners, and has been able to aggressively recapture margin dollars despite suppressed revenue. Consolidating leadership with Scott will generate improved operating efficiencies and further institutionalize best practices across our teams.

Our Insurance segment generated a 42% segment margin, growing segment profit by 10% YoY despite a 29% decline in revenue. As anticipated, several of our largest partners reduced marketing spend during the quarter due to disappointing loss cost trends in personal auto underwriting. Elevated inflation in the price of replacement parts and used car values, as well as the increased cost and limited availability of auto repair labor, have continued to outweigh the significant premium rate increases insurers have been securing. Until our partners have more visibility into the profitability of rates they are able to charge customers, we expect the desire to attract new policyholders will remain subdued.

Our Consumer segment earned a healthy 49% segment margin during the quarter, as revenue declined 22% YoY and segment profit declining a lesser 9%. Our lending partners have generally continued to tighten underwriting criteria, putting further pressure on loan close rates. Higher interest rates have also begun to reduce customer demand for personal and small business loans. The Credit Card business benefited from the completion of our Lightspeed implementation. Combined with the ongoing migration

of customer traffic to the LendingTree website as we sunset our CompareCards brand, we have built a solid foundation to grow our credit card offering going forward.

The Home segment continues to weather an unprecedented period of decreased consumer demand for mortgage loans. Margins have held up well despite the persistently low customer volume we are receiving. The national 30-year mortgage rate currently sits just below 7%, while 91% of homeowners have a mortgage with a rate below 5% today. This lock-in effect has led to reduced supply of existing homes for sale to record lows, slowing purchase mortgage applications and further reduced refinancing demand. Home Equity continues to be a relative bright spot, but as a floating-rate loan the continued increase in short-term rates driven by the Fed has started to reduce demand given the elevated cost.

Although we maintain a cautious view of the revenue opportunity ahead of us, we have effectively right- sized our business to operate profitably despite the various economic headwinds. Our targeted investments in the new MyLT experience, TreeQual, and a select group of internal projects should all drive positive returns as we complete them. We remain focused on serving our customers and partners through this tumultuous period, and establishing a strong base to grow the company with substantial operating leverage when revenue improves.

SUMMARY CONSOLIDATED FINANCIALS

1. Represents the portion of selling and marketing expense attributable to variable costs paid for advertising, direct marketing and related expenses. Excludes overhead, fixed costs and personnel-related expenses.
2. Variable marketing expense, variable marketing margin, variable marketing margin % of revenue, adjusted EBITDA, adjusted EBITDA % of revenue, adjusted net income (loss) and adjusted net income (loss) per share are non-GAAP measures. Please see "LendingTree's Reconciliation of Non-GAAP Measures to GAAP" and "LendingTree's Principles of Financial Reporting" below for more information.

Q2 2023 CONSOLIDATED RESULTS

Consolidated revenue of $182.5 million declined 30% over the prior year, driven by a 44% decline in Home revenue, a 29% decrease in Insurance revenue, and a 22% decline in Consumer.

We recorded GAAP net income of $(0.1) million or $(0.01) per diluted share. Included in that number is a $3.6 million restructuring and severance charge related to the closure of the Ovation credit services business and the expense reduction in March, which completes the charges we expect from these actions.

Variable Marketing Margin of $76.5 million declined 16% over prior year, as improved margins in Insurance and Consumer from last year helped to offset some of overall revenue decline.

Adjusted EBITDA was $26.7 million, generating a 15% margin.

Adjusted net income of $14.7 million translates to $1.14 per share.

SEGMENT RESULTS

1. The Home segment includes the following products: purchase mortgage, refinance mortgage, and home equity loans. We ceased offering reverse mortgage loans in Q4 2022.
2. The Consumer segment includes the following products: credit cards, personal loans, small business loans, student loans, auto loans, deposit accounts, and other credit products such as credit repair and debt settlement.
3. The Insurance segment consists of insurance quote products and sales of insurance policies.
4. The Other category primarily includes marketing revenue and related expenses not allocated to a specific segment.
5. Brand marketing expense represents the portion of selling and marketing expense attributable to variable costs paid for advertising, direct marketing and related expenses that are not assignable to the segments' products. This measure excludes overhead, fixed costs and personnel-related expenses.