On Tuesday, he blasted out the assessment from @SexCounseling that "The people are happy with President Trump and they see how poorly he is being treated" to @realDonaldTrump's 72.4 million Twitter followers. His retweet has itself been retweeted 6000 times.
It is not clear what attracted Trump to Michael's posts, but she appears among a circle of conservative pro-Trump Twitter users who regularly retweet one another. It is also not clear whether the name of her Twitter account had any bearing on Trump's decision to retweet her.
Michael's account links to her YouTube channel and a video about "Couples Sensual Touching" that might be best described as R-rated.
On her website, "thehappyspouse.com," Michael calls herself "a nationally recognised relationship expert and certified clinical sexologist."
"My mission is to help you resolve problems with your intimate life. With 20 years of counselling experience, I have helped thousands of people improve their quality of life and marriage," Michael says.
She claims advanced degrees or certifications from the Institute for Advanced Studies in Human Sexuality and The American College of Sexologists. Neither are accredited by the American Psychological Association, spokeswoman Kim Mills said. The APA does not police who calls themselves a sex therapist or a "Certified Sexologist," as Michael's LinkedIn profile identifies her.
Michael did not respond to requests for comment by phone and email.
Early in his presidency, Trump would post tweets but rarely responded or looked to Twitter for information. His staff would periodically bring him reports on how well tweets had done and would show him particularly friendly things to repost, according to a senior Administration official.
But it became "both an entrance and an exit" in 2018, as he would, on his own, dive through his replies to see who was praising him.
An aide said Trump has sometimes been taken aback by backlash to his retweets. Often, a string of retweets is not some grand statement - it's just Trump scrolling and clicking, people close to the President said.
"If he sees it and it's positive about him, he just posts it," the Administration official said. "It would never dawn on him to check and see who the person is."
He also likes to use retweets to force journalists and critics to reckon with the size of his Twitter following, current and former officials said. For example, after a firefighters union endorsed Joe Biden last year, Trump went on a barrage of early-morning posts, amplifying firefighters who praised him instead.
Trump has mused to aides that he can mix it up on Twitter more than in real life - and "kind of just see how it goes," a former senior Administration official said. And there are accounts he somewhat regularly looks at for retweet potential, aides say.
But Trump has conceded in the past that he was a little too quick to hit the retweet button.
"A lot of the times, the bigger problem is the retweets," he said last year to C-SPAN political editor Steve Scully. "You know, you retweet something that sounds good, but it turns out to be from a player that's not the best player in the world. And that sort of causes a problem."
Trump's taste in retweets is varied. A recent selection of retweets includes the conservative legal group Judicial Watch and ABC News journalist Jon Karl. He has retweeted official Republican accounts alongside @RedPillReport, which posts pro-Trump material and conservative views that are sometimes racially tinged or sexually suggestive.
"Red-Pilling" is a term that comes from the movie The Matrix and refers to a choice between a red pill that opens one's eyes to an ugly reality and a blue pill that does not.
@RedPillReport returned the favour yesterday, retweeting and commenting upon a Trump insult directed at Democratic presidential candidate Mike Bloomberg.
"When a President can make you laugh ... and fatten your 401K ... you know you've got the right man!" the post said.
Trump has sometimes retweeted posts from accounts that were later suspended, or accounts that said they were associated with the Q-Anon conspiracy group.
Dawn Michael is not among the 47 people Trump himself follows on Twitter. Nor are any of the other otherwise little-known people he has retweeted recently. The common denominator is always either expressions of support for Trump or criticism of his adversaries.
Prasad Vana, an assistant professor at Dartmouth's Tuck School of Business, has studied online marketing techniques and said that retweeting is marketing of a sort.
"In general the idea is to show that there is some consensus developing around an idea and so it's a way of saying, 'See? It's not just me, it's others who think like that.' That is primarily the intention."
Often, content that shocks or outrages is the most popular online, Vana said. That is not necessarily Trump's intent, but a president retweeting an account called @SexCounseling might raise eyebrows, he said.
"We probably are biased more toward content that agrees with our own opinions, but when you're on a big stage it is rather wise to vet some information before you put it out there," Vana said.