Leon Bennett/FilmMagic
<amp-jwplayer data-media-id="heHHwCgD" data-player-id="AHLj8qWB" layout="responsive" width="16" height="9" class="i-amphtml-layout-responsive i-amphtml-layout-size-defined i-amphtml-element i-amphtml-media-component i-amphtml-video-interface i-amphtml-built i-amphtml-layout" i-amphtml-layout="responsive"><iframe width="640px" height="360px" frameborder="0" allowfullscreen="" src="https://content.jwplatform.com/players/"heHHwCgD"-AHLj8qWB.html?isAMP=true" class="i-amphtml-fill-content" scrolling="no" style="overflow: hidden;"></iframe></amp-jwplayer><amp-analytics type="googleanalytics" data-credentials="include">
 <script type="application/json">
 {
 "vars": {
 "account": "UA-51932734-1"
 },
 "triggers": {
 "eventTriggerName": {
 "on": "video-play",
 "request": "event",
 "selector": "#myVideo",
 "vars": {
 "eventCategory": "video-events",
 "eventAction": "video-play"
 }
 }
 }
 }
 </script>
</amp-analytics><div id='jwppp-video-box-1389101' class='jwppp-video-box' ='video' ='http://schema.org/VideoObject' data-video='1' style="margin: 1rem 0;">
<meta ='name' content='Usher Steps In And Talks The State of R&;B, &#039;Confessions&#039; Turning 20, What&#039;s Next And More | Stepping Into The Shade Room'/>
<meta ='description' content='The king of &#039;Confessions&#039; himself, Usher, is Stepping Into The Shade Room to talk about everything from his most iconic albums, who he wants to work with next, his Las Vegas residency so far, and much more!'/>
<meta ='thumbnailUrl' content='https://dev.theshaderoom.com/wp-content/uploads/2023/08/Usher-Details-His-Most-Difficult-Life-Lesson-scaled-e1691178819471.jpg?w=768'/>
<meta ='uploadDate' content='2023-08-04T12:52:08-07:00'/>
<meta ='contentUrl' content='https://cdn.jwplayer.com/v2/media/heHHwCgD'/>
<div id='jwppp-video-1389101' class='jwplayer'>Loading the player...</div>
<script type='text/javascript'>
var playerInstance_1389101 = jwplayer( "jwppp-video-1389101" );
playerInstance_1389101.setup({
playlist: "https://cdn.jwplayer.com/v2/media/heHHwCgD",
})
</script></div><p>Usher is getting candid while reflecting on his upbringing, romantic relationships, and life lessons.</p>
<h5 style="text-align: center;">RELATED: <a href="https://dev.theshaderoom.com/tlc-chilli-past-relationship-usher/" target="_blank" rel="noopener">Chilli Reflects On Past Relationship With Usher &; Difficulty They Shared Moving On</a></h5>
<h3 style="text-align: center;">Usher Reflects On The &#8220;Hardest Thing&#8221; He&#8217;s Ever &#8220;Had To Do&#8221;</h3>
<p>&#8220;The King of R&;B&#8221; sat down for an exclusive interview with <a href="https://www.vibe.com/features/digital-covers/usher-king-of-rnb-vibe-cover-story-1234776425/" target="_blank" rel="noopener">VIBE</a> and opened up about his Vegas residency and decades-long career. During the conversation, the 44-year-old transparently reflected on the &#8220;most difficult&#8221; lesson he&#8217;s learned over the years.</p>
<blockquote><p>&#8220;I think the hardest thing that I’ve ever had to do was be single,&#8221; the singer explained before pondering in silence.</p></blockquote>
<p>Continuing the conversation, Usher added that he doesn&#8217;t like &#8220;being alone&#8221; and began to reflect on his upbringing.</p>
<blockquote><p>&#8220;The idea of creating a life with someone is what I would like to do, maybe because I didn’t have or didn’t see that. And I get to remedy that idea by having an incredible partnership. I can then have the thing that I ultimately wanted to see.&#8221;</p></blockquote>
<h3 style="text-align: center;">The Singer Talks &#8220;Healing&#8221; &; What Helped Him To &#8220;Be Able To&#8221; Be By Himself</h3>
<p>As the conversation continued, the singer explained that &#8220;healing took a lot,&#8221; and &#8220;looking back,&#8221; he believes he was suffering from &#8220;not necessarily having the kind of love&#8221; that he &#8220;wanted as a kid.&#8221;</p>
<blockquote><p>&#8220;Maybe I was suffering a lot from — just maybe not necessarily having the kind of love that I would’ve wanted as a kid. And wanting to figure out what that was all about. I didn’t have that relationship that I would’ve wanted to have with my father. And that the relationship that I had with my mother was slowly beginning to be under pressure. Because one, we were working together. Two, we had our differences. Three, I was getting older, but I think it was just life lessons&#8230;&#8221;</p></blockquote>
<p>Usher then shared the resource that ultimately helped him.</p>
<blockquote><p>&#8220;The therapy really did help me be able to be by myself.&#8221;</p></blockquote>
<h3 style="text-align: center;">Usher&#8217;s Superstar Ex, Chilli, Recently Reflected On Their Relationship</h3>
<p>As <a href="https://dev.theshaderoom.com/tlc-chilli-past-relationship-usher/" target="_blank" rel="noopener">The Shade Room</a> previously reported, Usher isn&#8217;t the only one looking back on earlier days. In June, the singer&#8217;s ex, Rozanda &#8220;Chill&#8221; Thomas, explained that it was for them to move from one another after their brief relationship in the early 2000s.</p>
<blockquote><p>&#8220;I love hard. I was like, ‘God, why can’t I get over this?’ He couldn’t either.&#8221;</p></blockquote>
<p>At the time, Chilli explained that she would prevent herself from participating in the dating pool due to her ongoing ties to the &#8220;OMG&#8221; singer.</p>
<blockquote><p>&#8220;I even stopped dating. Because before that I thought if I met the right guy during that time that I wasn’t over [Usher] it wouldn’t work. I would never want to straddle the fence.&#8221;</p></blockquote>
<p>Fortunately, things worked out for both parties. Chilli is now dating actor Mathew Lawrence, and Usher is going strong with his partner Jennifer Goicoechea.</p>
<p><amp-instagram data-shortcode="CdT8lBXONRJ" layout="responsive" width="600" height="600" data-captioned></amp-instagram></p>
<p>Additionally, the couple share two children, a son, and a daughter, while Usher is also the father to two children from his prior marriage to Tameka Foster.</p>
<p><amp-instagram data-shortcode="CtsOAv-OZ-Q" layout="responsive" width="600" height="600" data-captioned></amp-instagram></p>
<p>Roomies, what do you think of Usher&#8217;s sentiments and transparency? If you want to hear more from the star, check out his recent &#8216;Stepping Into The Shade Room&#8217; episode below!</p>
<p><amp-youtube data-videoid="QJ7aDiBcQ0I" layout="responsive" width="1000" height="563" dock="#dock-slot"></amp-youtube></p>
<p> ;</p>
 <div class="wpra-reactions-wrap wpra-plugin-container" style="justify-content: center;;"> <div class="wpra-reactions-container" data-ver="1.3.10" data-post_id="138910" data-show_count="true" data-enable_share="onclick" data-behavior="regular" data-animation="true" data-share_url="https://dev.theshaderoom.com/usher-most-difficult-life-single/" data-secure="40a47892f0"> <div class="wpra-call-to-action" style="color: #000000;font-size: 25px;font-weight: 600;">What Do You Think Roomies?</div> <div class="wpra-reactions wpra-static-emojis size-medium" style="border-color: #ffffff;border-width: 0px;border-radius: 50px;border-style: solid;background: #ffffff;">					<div class="emoji-8 wpra-reaction wpra-pad-fix" data-count="" data-emoji_id="8"> <div class="wpra-plus-one">+1</div>	 <div style="background-color: #ff0015" class="wpra-arrow-badge arrow-bottom-left hide-count"> <span style="border-top-color: #ff0015" class="tail"></span> <span style="color: #ffffff" class="count-num">0</span> </div>	</div><div class="emoji-10 wpra-reaction wpra-pad-fix" data-count="" data-emoji_id="10"> <div class="wpra-plus-one">+1</div>	 <div style="background-color: #ff0015" class="wpra-arrow-badge arrow-bottom-left hide-count"> <span style="border-top-color: #ff0015" class="tail"></span> <span style="color: #ffffff" class="count-num">0</span> </div>	</div><div class="emoji-4 wpra-reaction" data-count="" data-emoji_id="4"> <div class="wpra-plus-one">+1</div>	 <div style="background-color: #ff0015" class="wpra-arrow-badge arrow-bottom-left hide-count"> <span style="border-top-color: #ff0015" class="tail"></span> <span style="color: #ffffff" class="count-num">0</span> </div>	</div><div class="emoji-5 wpra-reaction" data-count="" data-emoji_id="5"> <div class="wpra-plus-one">+1</div>	 <div style="background-color: #ff0015" class="wpra-arrow-badge arrow-bottom-left hide-count"> <span style="border-top-color: #ff0015" class="tail"></span> <span style="color: #ffffff" class="count-num">0</span> </div>	</div><div class="emoji-2 wpra-reaction" data-count="" data-emoji_id="2"> <div class="wpra-plus-one">+1</div>	 <div style="background-color: #ff0015" class="wpra-arrow-badge arrow-bottom-left hide-count"> <span style="border-top-color: #ff0015" class="tail"></span> <span style="color: #ffffff" class="count-num">0</span> </div>	</div><div class="emoji-7 wpra-reaction" data-count="" data-emoji_id="7"> <div class="wpra-plus-one">+1</div>	 <div style="background-color: #ff0015" class="wpra-arrow-badge arrow-bottom-left hide-count"> <span style="border-top-color: #ff0015" class="tail"></span> <span style="color: #ffffff" class="count-num">0</span> </div>	</div><div class="emoji-12 wpra-reaction" data-count="" data-emoji_id="12"> <div class="wpra-plus-one">+1</div>	 <div style="background-color: #ff0015" class="wpra-arrow-badge arrow-bottom-left hide-count"> <span style="border-top-color: #ff0015" class="tail"></span> <span style="color: #ffffff" class="count-num">0</span> </div>	</div> </div> <div class="wpra-share-wrap wpra-share-buttons-bordered" style="">				 </div> <!-- end of share buttons -->			 </div> <!-- end of reactions container --> </div> <!-- end of reactions wrap -->