The 50-plus generation find there are still many of the same stigmas associated with meeting people online as there are for younger generations. These are the same questions going through first dates' heads, no matter their age.
Will I need my friend to ring half way through with an 'excuse' for me to leave promptly?
They estimate that 542 people get married every day in the USA having met on their website, accounting for nearly 5pc of new US marriages.
According to a You Gov Survey last year, one in five relationships in the UK now start online, with UK singles contributing almost £3.4bn annually to the economy in their search for a partner.
With some 5.8m people over 45 living alone and some 1.7m women over 65 who are widowed in the UK, online dating for the over-50s has become big business.
Having proven the concept - being certain there was both a need and commercial value - Matt went about building a team to assist him with the creation of the site.
The US dating services industry has performed well over the last five years.
His single mother asked him why he couldn't help her find her knight in shining armour, and so he literally went about it.
Revenue gains averaged 3.5pc per year over the five-year period to reach bn (£1.25bn) in 2012, with consumers increasingly turning to the internet to meet prospective dates.
America is home to dating giants such as e Harmony, who have has been profitable since 2004 and exceeded the bn in revenue mark in 2009.
New entrant my Lovely goes live on Friday, with a business proposition aimed at those over 50s.
Matt Connolly conceived the idea of the website to dispel the stigma and solve a problem presented to him around the Sunday lunch table.
He signed himself up to a number of "senior dating" sites and interviewed hundreds of single men and women.
What he found was that even though this is one of the fastest growing demographics of single people, most would never consider online dating without their child's encouragement.