There are 2 books in the Wingmen Inc. series. The newest book is The Matchmaker's Replacement which came out in 2016.

1
The Matchmaker's Playbook

Book cover of The Matchmaker's Playbook
Wingman rule number one: don't fall for a client.

After a career-ending accident, former NFL recruit Ian Hunter is back on campus-and he's ready to get his new game on. As one of the masterminds behind Wingmen, Inc., a successful and secretive word-of-mouth dating service, he's putting his extensive skills…
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2
The Matchmaker's Replacement

Book cover of The Matchmaker's Replacement
Wingman rule number two: never reveal how much you want them.

Lex hates Gabi. Gabi hates Lex. But, hey, at least the hate is mutual, right? All Lex has to do is survive the next few weeks training Gabi in all the ways of Wingmen Inc. and then he can…