Matt Reardon, the oldest son of a large family, grew up in Flint, Michigan. Disapproving of his father, Sean, because of Sean's many affairs, Matt finally left home as soon as he could to find happiness somewhere else. In 1994, a 25-years-old Matt went to a bar in Indiana and hid from the police. He slept with a blonde woman and she covered for him when the police arrived. The reason that Matt was hiding was that he was wanted for car theft and attempt to do bodily harm. Matt was innocent but couldn't prove it because a powerful man had accused him of the crimes and everyone believed him. At this point, Matt met an older woman, who arrived in Indiana to clear her head. He followed her to her ship at Summit Lake and when he went to a bar, the woman was already there, playing a poker game with some locals. When a man played unfair, the woman threw her beer onto his face and the man got violent, so Matt rescued the woman by punching the man and throwing him out. Later, Matt stowed away on a sailboat that the woman had rented. Though upset at seeing him, the woman befriended Matt, who called himself "Buster". He didn't know the woman's name and simply called her "Contessa". In the evening, Matt reappeared at "Contessa's" door because he needed a job. "Contessa" let him sleep outside and hired him to make repairs on her cottage. A few days later, before Contessa returned home, she ignored storm warnings and went sailing again. A worried Matt followed her with a motorboat but when her sailboat capsized and Contessa was about to drown, Matt saved her and brought her to a nearby island. The couple became closer in the cave and made love after a few days. Finally, Josh Lewis arrived with the helicopter to save Contessa (whose real name was Vanessa) and Matt disappeared.

However, to Matt's surprise, Vanessa didn't go home with Josh because she wanted to find Matt first. Unfortunately, when she did, she told him that he was too young for her and the couple said goodbye. Saddened, Matt decided to go to Springfield to visit his little sister, Bridget, whom he hadn't seen for six years. He hitched a ride with trucker Caroll O'Malley. As they arrived at a warehouse, a masked man suddenly attacked Caroll and Bridget's boyfriend, Dylan Lewis, and stole the truck. Having witnessed the entire thing while hiding out, Matt jumped out of the truck and lost the scrimshaw key chain that Contessa had given him. Though the masked men fired some shots at Matt, they didn't follow him and Matt arrived unharmed at the Reardon Boarding house. There he anonymously called the police and learned that the police had found Dylan and Caroll. As for Bridget, she introduced Matt to her friends and though Matt wanted to leave town again, Bridget and Dylan convinced him to stay, with Dylan offering Matt job at Lewis Construction.

On his first day at work, Matt used the bulldozer and, when the shovel broke, Dylan realized that one of his workers was a saboteur , Meanwhile, family and friends tried to introduce Matt to Vanessa Chamberlain but circumstances prevent them from meeting, which didn't upset Matt too much since he assumed that she was a spoiled rich woman. Finally, Vanessa arranged a family dinner at the Country Club just for Matt and when Matt arrived, he was shocked to see that Vanessa was none other than his Contessa! Vanessa was surprised, too, and though Matt wanted them to revive their relationship, Vanessa was hesitant despite her love for him. She was afraid of the people's reaction but Matt thought she was ashamed of him. Not knowing about their connection, Dylan hired Matt to do some work at Vanessa's house. When Vanessa remained hesitant, Matt decided to leave town and told her goodbye. Before he left, he sneaked into Vanessa's room to say goodbye to her one more time but Vanessa wasn't home. While writing Vanessa a goodbye-letter, Matt took a pill for his headache. Unfortunately, it was a sleeping pill and knocked him out.

When Vanessa found him the following morning, she helped him and the couple finally renewed their romance in secrecy. Meanwhile, Dylan ordered his workers to do a health check but since Vanessa didn't want him to learn that she and Matt were at Summit Lake at the same time, Matt destroyed his personal file. Unfortunately, the scrimshaw key chain that was found at the crime scene, and the fact that Caroll recognized Matt as the hitchhiker, led many to believe that Matt was in cahoots with the masked men. As a result, Dylan, Josh, Caroll and Frank Cooper confronted Matt at a warehouse with Vanessa and Bridget in attendance. Though Matt could have been able to prove his innocence with Vanessa as his alibi, he kept quiet to protect her and looked utterly guilty. In addition, Frank confronted Matt about his previous crime of car theft and bodily harm and Matt left town to prove his innocence. He hid at the Bauer cabin until Ed Bauer and Eve Guthrie arrived. Later, Vanessa found him outside and when the couple met at the docks, Matt learned that Gabriella Lopez was uncovered as a spy of the masked men.

Back in town, a now vindicated Matt had to deal with Dylan's blindness as well as Alan Spaulding. Alan had learned, through a listening device, of Matt and Vanessa's affair and tried to blackmail Vanessa with it so that she would help him to get power back at Spaulding. Meanwhile, Matt was dismayed that Vanessa still refused to make public their relationship and though he considered leaving town again, he built a hiding place for them instead at 5th Street. They met at this place a few times in secret but one time, Matt found Vanessa's son, Bil,l in his car and Bill confessed that he was jealous of Matt because Michelle Bauer had a crush on him and Bill wanted to prove to Michelle that Matt was carrying on an affair. Matt brought Bill home and got him to stop spying on him by giving him tips of how to act toward Michelle. However, not long after, Josh caught Matt and Vanessa in their place and accused Matt of only wanting Vanessa's money. Though Matt denied it, Josh insisted that he would only hurt Vanessa and Matt again considered leaving town until Vanessa stopped him. On New Year's 1995, Matt and Vanessa planned to meet at their place again but Matt arrived late when suddenly there was a fire at 5th Street. Believing Matt to be dead, Vanessa was so thrilled to see him alive that she ran to him and kissed him in front of everyone. As a result, everyone learned about the relationship and the press slammed Vanessa due to Matt's younger age. Matt and Vanessa also had to deal with disapproval from Bridget, Bill and Vanessa's father, Henry Chamberlain. Not long after, Bill confessed that he accidentally caused the fire because he had found out about the affair and had destroyed Matt and Vanessa's place.

. Not long after, Matt met a spoiled young woman who told him that she was about to get as much money as she could from her parents. Later, Matt met the young woman again and was shocked to learn that she was none other than Vanessa and Ross's daughter, Dinah Marler. Though Dinah claimed that she had only been joking during their talk, Matt didn't believe her and thought that Dinah wanted to get her trust fund from Vanessa. Matt kept quiet about this fact until Dinah caught him naked at the boardinghouse one day and Matt realized that Dinah wanted to cause trouble for him and Vanessa. Things got more complicated when Matt, encouraged by HB Lewis, proposed to Vanessa and she turned him down. Meanwhile, Josh wanted to revive Lewis Construction and rebuild 5th Street and Matt agreed to work for him since he realized that Josh was asking because he truly wanted Matt's help and not just because of Vanessa. Later, Matt proposed to Vanessa again and, after seeing how well he helped Bill and Michelle Bauer following Eve Guthrie's death, she agreed. As for Dinah, she still schemed to separate the couple, this time by poisoning Bill against Matt. Dinah sneaked naked into the bathroom to seduce Matt but Matt rudely turned her down and convinced Vanessa that Dinah had set everything up. Meanwhile, Matt had to deal with Bridget because she neglected her son Peter due to her new relationship with a rocker named Skunk. Matt disapproved of Bridget's refusal to tell Skunk about Peter because he didn't like children, so Matt arranged for Skunk to see Peter and Skunk left Bridget as a result. In the meantime, Sean, whom Matt hadn't seen in ten years, came to town, Matt was not happy to see his father since he, rightly, believed that Sean's real reason for the visit was to get money for one of his unsuccessful business ideas.

. Later, when Sean talked about the "good old days" during a family dinner at the Country Club, Matt exploded and brought Sean outside. He then blasted Sean for once using Matt as his alibi for Sean's affairs with other women in cheap hotels. Sean denied it until Matt confessed to him that he had once eavesdropped on one of his "meetings'. Unfortunately, Bridget overheard the conversation and Matt ordered Sean to leave town. In the meantime, Dinah asked Matt for help because a man named Victor was threatening her about returning his money, but Matt ignored her because she had brought Sean to town in the first place. Suddenly, Dinah was kidnapped by Victor but Matt and Ross's wife, Blake Marler, thought that Dinah had set up her own kidnapping to get money. Later, Dinah announced, via tape recorder, that Victor wanted $ 2 million in ransom money and Matt, to prevent Vanessa from bringing the money to Victor, decided to take matters into his own hands by rescuing Dinah. He was able to locate her in a cheap hotel and climbed through the window to Dinah. Unfortunately, when he tried to escape with her, Victor caught them and tied them up in a cave. There, Dinah confessed to Matt that she had arranged her own kidnapping to save Peter because Victor had threatened to kidnap him. Though angry, Matt forgave Dinah because she had saved Peter. They were able to get untied but Victor caught and tied them up again in an abandoned train, while the police found the old place abandoned. Not long after, Victor got the ransom money and freed Dinah, but escaped with a still kidnapped Matt. Finally, Roger Thorpe placed bees in the car and a panicked Victor caused an accident during a fight with Matt and was arrested. Now free, Matt told everything to Det. Patrick Cutter but kept quiet about Dinah's cooperation with Victor.

In the meantime, Matt and Dinah slowly bonded and, though Matt covered for her crimes, he later told Ross everything to save Ross and Blake's marriage, while Dinah herself told Vanessa everything because she thought Ross and Matt would inform her anyway. Meanwhile, Matt had to deal with Vanessa's feud with Roger Thorpe because Roger was involved with Dinah and Vanessa threatened to prevent Roger from seeing Peter if he wouldn't leave Dinah. To end the feud, Matt offered to get Dinah her trust fund if she left Roger, married someone else and left town. However, Vanessa disapproved of Matt's actions and their relationship got so strained that their upcoming wedding was in danger. Finally, Vanessa realized, with Matt's help, that she should no longer intervene in Dinah's life and the couple made up. As for Dinah, she suddenly invited her family to the Country Club to marry Marcus Williams so she would get her trust fund, but Roger arrived in time to stop her and convinced her that he was the right man for her. Dinah agreed to marry Roger on the spot but Matt and Vanessa condemned the wedding by leaving. At this point, Vanessa and Matt concentrated on their own wedding and Matt insisted on signing in a pre-nuptial agreement. Though the wedding began as a success, it ended in a disaster that included a ruined wedding dress and food poisoning.

Not long after, Amanda Spaulding returned to town and Matt was shocked to recognize her as Mandy Harper whom he had known back in Malibu, California. He and Amanda agreed to hide their secret from everyone but when Matt realized that Amanda wanted to get Ross, who was her old lover, back for herself, Matt told Amanda to leave Ross alone or else he would expose her secret. Unfortunately, Amanda continued to scheme to get Ross and, in 1996, Matt again threatened to expose her secret despite the fact that Matt knew the truth would hurt Vanessa. One day, Matt was shocked to find an unconscious Amanda at the construction site and brought her to Cedars. Blake had locked her up and though Amanda pressed charges against Blake, Matt forced her to drop them and threatened to tell Ross her secret if he found out that Amanda had set Blake up. Later, Matt found out that Amanda had escaped from the construction site and had met Dinah in a bar, only to return in order to set Blake up. Later, when Blake arrived to tell Matt and Vanessa that she just spotted Ross kissing Amanda at the Bauer cabin, Matt had enough and went to the cabin and told Ross about Amanda's schemes as well as her dark secret as well as his: Matt had once worked as a male escort for Amanda in Malibu! His job had been to "make older woman happy". The following day, Matt revealed his secret to Vanessa before Amanda was able to and further confessed that their first meeting in Summit Lake wasn't pure chance. He had been paid to "look after" Vanessa but claimed that he had fallen in love with her for real. A shocked Vanessa didn't know if she could forgive Matt and distanced herself from him. However, when Vanessa's father died, Matt comforted her and the couple made up.

Meanwhile, Buzz Cooper and Alan-Michael Spaulding wanted to expose Amanda's past during a press conference in order to stop Alan's plans to demolish 5th Street. Vanessa herself encouraged Matt to go to the press conference to confirm everything. Unfortunately, the public exposure of Matt's past got Bill so angry that he accused Matt of only marrying Vanessa for her money. Apparently, Bill had found a check for $ 200,000 that Vanessa had signed for Matt. Matt didn't know about the check and was surprised when Vanessa told him that it was for Bill because she had chosen Matt as Bill's guardian if something ever happened to her.

Meanwhile, Matt bought some land at Lake Summit as a surprise for Vanessa and had plans to build a house for them there and dreamt of the perfect life at the island. As the same time, Vanessa began to have dizzy spells and though she claimed that everything was okay, Matt believed that she was hiding something from him and that the mysterious Zach Smith knew more about it. Suddenly, Vanessa had a car accident and when Matt rushed to the scene with Dinah and Bill, the cops stopped him and the car exploded. Vanessa's wedding ring was found in the burned car and, although everyone else was convinced that Vanessa was dead, a heartbroken Matt had the feeling that she was alive. At Vanessa's funeral, Matt met her ex-husband, Billy Lewis, for the first time while Bill wanted to leave home because he disapproved of Matt as his guardian. In addition, Bill faked Matt's signature to get the $ 200,000 but Matt, Nola and Quint Chamberlain caught and stopped him, whereupon Bill moved into the boardinghouse. Meanwhile, Matt felt lost without Vanessa, he lost the will to live and people around him soon realized it. In the meantime, Matt became more and more skeptical about Zach and believed that he knew something about Vanessa. Matt went to talk with Zach at the lighthouse and when Zach wasn't there, Matt broke in and found a letter that Vanessa had wrote to Matt. Though Zach was able to explain everything, Matt remained skeptical and asked Frank to investigate Zach. Although his family tried to get him to move on, with Nola even setting him up with a widow named Alice and a woman named Natasha, Matt wasn't ready to give up on the slim chance that Vanessa was alive. As for Bill, he continued to act out and during a brawl with him, Matt finally got him to admit that Bill wished that Matt was dead instead of Vanessa. This confession brought Matt and Bill closer together.

Not long after, Matt tried to help Bill when a girl named Candy stated that she couldn't go out with him because her mother forbade it. Trying to help, Matt had lunch with the woman and was disturbed to learn that he was the reason. The woman had gotten wind of Matt's former life as a gigolo and didn't want her daughter exposed to a man like that. Although Matt tried to convince the woman not to punish Bill for something he did long ago, the woman still refused to allow the two teens to date. Unfortunately, when Bill learned about what happened, he turned away from Matt. In 1997, Matt tried to be the supportive stepfather and give advice to Dinah about her failed relationship with Hart Jessup. Although he tried to get her to see that she was a special woman who'd find a man to love her for who she was, Dinah wasn't quite convinced. Depressed over the loss of her mother and Hart, Dinah bonded with Matt over their shared loss and their attempts to build a children's wing at Cedar's in Vanessa's memory.

Knowing how much Dinah still loved Hart, and that the feeling was mutual, Matt arranged for the couple to be locked in a shed until they could settle their relationship one way or the other. Matt's plan worked and the pair decided that their love could overcome their differences. While he was helping everyone else with their problems, Matt continued to build his and Vanessa's dream house at Lake Summit. While building the house, he struck up an on-line friendship with a woman who called herself "Tess." Calling himself "Robert", Matt and the woman corresponded for weeks and formed a bond. Then one day, Matt saw the words "I miss you Matt." on his computer, and he knew instantly that he had been talking to Vanessa. Although Dinah initially scoffed at his theory that Vanessa faked her death (to spare her family the agony of dealing with her fatal illness), soon she began to suspect that perhaps he was right and she set out with Matt to locate Vanessa at a hospice in Switzerland. After Bill's high school graduation, Matt and Dinah traveled to Switzerland and although they found proof that Vanessa was alive, her illness had gone into remission and she'd already checked out!

Looking for clues, the pair learned that Vanessa had been treated by a doctor named Michael Burke, who had a questionable past. Looking for clues to Vanessa's whereabouts, they searched Michael's room and found a photo I.D. on one of his jackets and they both recognized him as having been at Bill's graduation. Thinking that Michael preyed on helpless women, Matt began to fear for Vanessa's safety. The pair then went back to Springfield to decide what to do next, but everything they did seemed to lead to a dead end. Soon Matt caught up with Michael Burke, but Vanessa had taken off shortly before that because she felt Michael was beginning to get feelings for her other than friendship. After learning that he was wrong about Michael, Matt allowed Michael to help him find Vanessa. Meanwhile, Dinah tried an on-air plea on television to convince Vanessa that there was nothing going on between her and Matt. However, Vanessa still would not return. Soon Matt decided that if he finished their dream house Vanessa would come home, so with the help of several other Springfield residents, Matt finished the house. They had a housewarming party and that night after everyone left, Matt was standing in the house when Vanessa finally returned home. Though Matt was angry that Vanessa didn't share her secret with him, he forgave her and the couple reunited.

Soon after, Vanessa began experiencing dizzy spells while Matt had to struggle with his feelings of resentment towards Vanessa for faking her own death. Matt soon forgave Vanessa but when he discovered she was still taking her medication he became worried and made her go to the doctor for fear of the disease coming back. Vanessa reluctantly went to the doctor. It was soon discovered that Vanessa was pregnant. Her doctors advised her not to carry the baby to term because her disease could come out of remission and kill her. After hearing the news, Matt became extremely worried about losing Vanessa because of the pregnancy and encouraged her to have an abortion. Vanessa, though, was determined to carry her baby to term. However, Matt was adamant that Vanessa not risk her life for her child's and almost convinced Vanessa. While Vanessa was at Cedars to terminate her pregnancy, Matt found a letter at home that Vanessa had written to her unborn child. At the hospital, Vanessa had a change of heart, and to her surprise, so did Matt when he rushed to Cedars to stop her.

In early 1998, a vindictive Dinah attempted to hurt Vanessa when Vanessa started a friendship with Dinah's chief rival, Cassie Layne. Dressing up like Vanessa, Dinah set it up to have Matt kiss her, setting it up so that her mother would see. However, the plan failed and Matt blasted Dinah for her actions. Meanwhile, Vanessa and Matt learned devastating news--the pregnancy was causing complications and threatening to cause her disease to return. Although the doctors suggested terminating the pregnancy by performing a C-Section, to Matt's horror, Vanessa refused to go through with the C-section, willing to let herself die so that the child live. Unwilling to let Vanessa die, Matt decided to take her to court to force her to have the procedure, rationalizing that he'd rather have her hate him and still be alive. Enraged that Matt was taking her decision way from her, Vanessa vowed to fight him. Fortunately, the problem became moot when Vanessa went into premature labor herself and gave birth to a beautiful baby girl who they named Maureen after Matt's aunt and Vanessa's late best friend, Maureen Bauer. Later, when Maureen, needed a kidney, Holly Reade saved her by donating part of hers. In appreciation, they made Holly the baby's godmother.

Later, Matt was surprised by Vanessa's decision to go back to work at Spaulding Enterprises. At the same time, Matt formed a friendship with Beth Raines and the two bonded over their children. Soon a lonely Beth started to become attracted to Matt and one night, when he drove a tipsy Beth home, she kissed him. An ashamed and guilt-ridden Beth apologized profusely to an understanding Matt, then talked to him about her loneliness and the lack of hope that she'll ever find a man. The next morning, after falling asleep at Beth's, Matt learned that Dinah had suffered a miscarriage and went to the hospital where he found an upset Vanessa. Although he tried to ease her mind about why he never came home, Vanessa suspected that Beth was after her husband and confronted her. The tension between Vanessa and Matt continued for several weeks, not only because of his friendship with Beth but also Vanessa's tendency to defend Dinah, who was acting irrationally. In the fall, Vanessa was bitten by a poisonous spider and immediately thought the culprit was Beth! Matt's dismissal of her suspicion (which turned out to be false anyway) further widened the gulf in their marriage. By year's end, things had gotten so bad that Vanessa suggested a brief separation. However, the plans changed when Maureen suddenly took her first steps. In 1999, things got complicated when Dinah was accused of murdering Hart and Vanessa hid her! Angry that Vanessa was covering for Dinah, Matt insisted that if she wouldn't turn Dinah in, he would. Finally he got Vanessa to admit that Dinah was hiding in the house, but when Matt went there, Dinah was nowhere to be found. Suddenly, both Beth and Matt saw Vanessa drive off with Dinah! While Matt tried to cover for his wife, Beth maintained that she wouldn't lie for Vanessa.

However, when Lizzie was kidnapped (and later found) a sympathetic Beth agreed to lie for Vanessa. Beth's willingness to protect Vanessa touched Matt and, after confiding in Beth that his marriage was probably over, he kissed her. Later, Matt, distraught when he believed that Vanessa stood him up at Towers, started drinking and flirting with a woman at the Towers bar and almost got in a fight with the woman's date before he was rescued by Beth. As they were leaving though, Vanessa, who was angry that Matt stood her up, spotted them. Realizing that there was a mix-up, Beth tried to set the record straight but didn't when Vanessa suddenly lashed out at her. Although Beth and Matt almost got passionate when she took him home, she couldn't go through with it and told him that there must have been a time mix-up; Vanessa didn't mean to stand him up. With that revelation, Matt went off to fix his marriage. Unfortunately, at this point, Vanessa was convinced her marriage was over and made plans to leave. Desperate to locate Vanessa, whom he finally learned was staying at the Bauer cabin, Matt rushed off to find her and slipped on ice at the cabin. Luckily for Matt, Vanessa found him and saved him. Now reunited with Matt, Vanessa decided to go to the police after all with Dinah's whereabouts, however, by this point, Dinah had disappeared.

Later, Matt had to deal with Bill's problems again when Bill was set up by Ben Warren to hack into the computers at Spaulding Enterprises. When Ben claimed that Bill acted alone, Matt responded by punching him. Not long after, Spaulding took over Lewis Oil and instead of working for Phillip Spaulding, Matt, Billy and Josh quit their jobs instead. In addition, Matt was horrified to learn that Vanessa's illness had returned because of the problems with Ben. While Matt tried to help Vanessa and shield her from her family's problems, she had a car accident that left her comatose on the same day that Ben was murdered. Throughout the next several weeks, Matt started confiding in mobster Carmen Santos, who seemed genuinely concerned for Vanessa's health. In January 2000, Vanessa woke up, called Carmen's name, and slipped into a coma again. Although sleeping pills were found in her blood and Rick Bauer questioned why Carmen was so worried about Vanessa, Matt defended Carmen. What Matt didn't know was that Carmen was Ben's real murderer and wanted Vanessa dead so that the prime suspect, Matt's cousin, Michelle, could be convicted of his murder. Matt accepted Carmen's gift of a lip balm for Vanessa, not realizing that the balm was poisoned.

Later, Matt was shocked to see Carmen's daughter, Pilar Santos, on television, confessing that it was Vanessa who accidentally fired the fatal shot. To protect Vanessa, while risking Michelle's conviction, Matt brought her to the cabin at Lake Summit. When Matt kissed Vanessa on her lips, he tasted the poison and was shocked when a nurse confirmed that the lip balm was indeed poisoned. After Matt stopped using it on her, Vanessa woke up. To further protect Vanessa, Matt vowed to never let her return to Springfield but Vanessa confessed to him that she had, indeed, found Ben bleeding from Carmen's shot and that she accidentally shot him to death when he had grabbed her. Vanessa wanted to return to testify for Michelle (who had already been convicted) and though Matt lied to her that Carmen had already been arrested, Vanessa realized the truth when Billy arrived. Though Matt and Billy wanted to convince Vanessa that a statement on video would be enough to help Michelle, Vanessa saw through their lies and Billy was able to convince Matt that Vanessa had to return to testify. Afterwards, Carmen was arrested and Michelle was cleared of all charges. In addition, Vanessa's illness went into remission again. Not long after, Vanessa received the distressing news that Dinah was pregnant. Anxious to help the wayward Dinah, Vanessa and Matt gave up their lives in Springfield to help her.

In 2004, Dinah returned to town. It was soon learned that Dinah miscarried her baby. In addition, it was discovered that at the time of Vanessa's last visit, Vanessa and Matt had no idea where exactly Dinah was. By early 2005, Dinah had been exonerated in Hart's death. Unfortunately, her resentment of Cassie had not abated and a worried Ross staged an intervention to convince her to leave town forever. Matt returned to town to help Ross, Blake, and Bill convince Dinah to do the right thing. Unfortunately, they only succeeded in angering Dinah further. The same night, Matt met Bill's new wife, the older Olivia Spencer, and then left for Europe. In 2006, Matt and Vanessa returned to help plan Dinah's wedding to AC Mallet. Though Vanessa was convinced that Dinah had matured, Matt was extremely skeptical and was certain that the wedding would never happen. After Dinah professed how much she loved Mallet. After Matt apologized for his negative attitude, and volunteered to walk Dinah down the aisle for Ross. Unfortunately, Matt turned out to be right after all. When Dinah learned that Mallet had been conducting surveillance on her for the FBI, she became enraged and cancelled the wedding. A month later, Vanessa shocked Dinah with the news that she, Matt, and Maureen were moving back to Springfield. This did not sit well with Dinah, who thought they were doing it to keep tabs on her.

In 2007, Matt sought out investors for a new business venture. At the same time, he and Vanessa were displeased with the arrival of old friend of Dinah's: Cyrus Foley. Cyrus and Dinah's were partners in crime in Europe and Vanessa was instrumental in Cyrus getting arrested. Now released from a Spanish jail, Cyrus feigned forgiveness and told everyone that the wanted to reform and even asked to be a part of Matt's new business. Of course, neither Matt nor Vanessa believed Cyrus's claims of being a changed man. Weeks later, Vanessa and Matt happily celebrated as Dinah and Mallet finally married. Unfortunately, things while Dinah's life was on the upswing, Matt's would begin to unravel. The Springfield PD had been keeping Cyrus under surveillance and Mallet became suspicious when large sums of money were being transferred out of Vanessa's account. Startled, Vanessa gave Mallet permission to investigate which made Matt very nervous.

Matt's nervousness wasn't lost on Dinah and when she inquired about it, he confessed that he dipped into her funds to woo investors and never replaced the money or told Vanessa. Weeks later, Matt was forced to admit the truth to Vanessa when his main investor began demanding his money. Sadly, the investor was nothing more than a loan shark and Vanessa berated Matt for being stupid enough to do business with a criminal, When Vanessa asked why he couldn't come to her, Matt confessed that throughout their marriage he always felt second-best. Since she was always the one with all the power, this was his chance to prove himself. Matt had another secret—he not only dipped into Vanessa's money; he used Maureen's trust fund as collateral. Incensed, Vanessa threw Matt out. A desperate Matt went to Dinah's demanding that she help him track down Cyrus and the money that Cyrus stole from Vanessa. As Matt was badgering Dinah to help him, Vanessa came to drop off Matt's bags—she was kicking him of their apartment. Though Dinah tried to intervene, Vanessa refused to cave in. As the days went by, Matt began feeling more and more sorry for himself and by the time Dinah visited him, he'd been drinking for a while and his place was a wreck. When Matt lamented that he was all alone, and began throwing things in frustration, Dinah assured him that she was on his side. While Matt continued to plead with Vanessa to take him back, he continued to get threats from the loan shark about his debt. Just as Vanessa started to forgive Matt, Mallet tried urging Matt to run away with his family to get away from the loan sharks for his own safety. Dinah walked in on the conversation and sternly told him to stay instead of running. Matt followed Dinah's advice and, soon after, Vanessa agreed to take him back.

At the same time, Mallet was approached by Griggs, his former boss and the loan shark who was after Matt. To protect Matt, Mallet and Matt set it up to look like he shot Matt and dumped the body n the water. Unfortunately, Matt was certain that one of Griggs's men saw him come out of the water and informed Dinah. Mallet and Dinah both went after Griggs and Dinah took a bullet meant for Mallet. As Dinah languished in a coma, Vanessa rebuffed Matt's concerned and told that taking him back was a huge mistake and she never wanted him to live with her again. When they began to argue, Mallet threw them out of the room. Out in the hall, a distraught Vanessa informed Matt that he should be in that bed instead of Dinah. When Vanessa refused to even talk to him, Matt announced that he was done apologizing and reiterated that everything he did he did out of love. Soon after, Dinah finally emerged from her coma. Unfortunately, her head injury left her confused and she continued having trouble with her memory. Though she tried to cover, she finally admitted the truth to Matt who helped her make a cheat sheet for herself and encouraged her to confide in Mallet. However, Dinah was unwilling to do so and continued to cover her condition. Days later, it became apparent that something was wrong when Dinah froze during a live television interview. Mallet quickly covered and Dinah was forced to come clean about her condition. In the meantime, Matt was saddened to receive divorce papers from Vanessa.

Days later, Dinah found a credit card and, instead of returning it, she used the card to buy drinks. Matt came across Dinah at the bar and not only played along with the ruse, but covered in front of Mallet. Suddenly, Dinah could have sworn that she saw Griggs but Matt assured her that Griggs was in prison. Seeing her distress, he suggested she have Mallet check on it. Mallet did and confirmed that Griggs was indeed in prison. The next day, Dinah had a bizarre hallucination in which she saw and shot Griggs. Suddenly, she saw him for real. Confused, Dinah went straight to Matt. Unfortunately, Matt had just had an argument with Vanessa who warned him to stay away from Dinah since she believed that he was a bad influence on her daughter. Though Matt tried to steer Dinah away from him, she confided that he was the only one she could confide it. When she offered to leave to keep him from getting in trouble with Vanessa, Matt realized that he needed her too and suddenly kissed her. He quickly pulled away and apologized but Dinah insisted that it was no big deal.

Weeks later, Matt saw Vanessa with Billy and told Dinah that since her mother moved on, that meant he could too. Realizing that he was hitting on her, Dinah let him down gently. Days later, Dinah called Matt and warned him that Vanessa was at a charity ball with Billy. Having had some drinks, Matt burst into the event and demanded to dance with Vanessa. When Billy stepped in, Matt started to cause a scene and called Billy a drunk and demanded that he not be allowed around his daughter. That same evening, Dinah met with Matt and came on to him. As they kissed passionately, Mallet saw the pair and immediately attacked Matt. Vanessa witnessed the entire scene as well. After her tirade, in which she blasted both Mallet and Vanessa, Matt told Dinah that the others bought her little performance. Cornered, Dinah confessed that she had to free Mallet from her since she was weighing him down financially. Later, Matt told Dinah that she was the only reason he stayed in town after his fight with Vanessa. Later, after a meeting with Mallet, Dinah unexpectedly pulled Matt into a kiss.

In the meantime, Vanessa and Mallet were both highly concerned with Dinah's well being, especially around Matt. Later, Dinah came for Matt for company again, however he was frustrated because he was supposed to spend time with Maureen but she was taking an entrance exam at her new boarding school. Feeling sorry for him, Dinah pulled Maureen out of school and brought her to Matt. Worried that Dinah was a danger to herself as well as others, Vanessa and Mallet had her committed to a mental hospital. Dinah called Matt, begging him to get her out but he refused by claiming to be speaking with Vanessa again. Dinah angrily branded him a traitor. Days later, Matt arrived at the hospital with Vanessa, giving the impression that they were back together. Months later, Matt confessed to Dinah, who'd since been released, that he and Vanessa were never together. It was all a lie to help Dinah get her life back together. After Dinah hugged Matt, he backed away and told her that they weren't good for each other anymore. Dinah was always looking for trouble and he did not need that.

In 2008, Dinah surprised Matt with news that, thanks to some successful investments, she was the new owner of the Spaulding mansion and hired him to redo the place. Later, when Dinah discussed the two of them picking up Maureen for dinner after school the next day, Matt made it clear that he had to check with Vanessa first. Matt's tip-toeing around Vanessa got to Dinah, and she became upset that Matt felt he had to clear her spending time with her own sister through Vanessa. Meanwhile, though she and Mallet were no longer together, it was clear that Dinah regretted pushing Mallet away. One day, while out with Matt in the park, Dinah spotted Mallet with Marina and used Matt to make Mallet jealous. Later, Matt expressed his discontent with Dinah for using him to upset Mallet and asked if the renovation was even real or was it a ploy. Dinah quickly apologized and assured him that the renovation project was very real.

In 2009, Matt continued to lead a solitary life. Discouraged, he asked Frank for advice on women. Though Matt considered asking Natalia Rivera out, Frank quickly shot down that since he was interested in Natalia. Later, Matt was a guest at Frank and Natalia's engagement party. Meanwhile, Matt continued his friendship with the Lewises and was with Billy and Josh when they learned of Bill's engagement to Lizzie. In addition to his own romantic woes, Matt spent his time trying to encourage both Frank and Josh to get out there and meet women. Meanwhile, Matt overheard Dinah admit that she killed the Edmund Winslow look-alike when she feared that he was going to go after Shayne Lewis's son. Dinah confessed the truth to Matt and talked about her unworthiness of marrying Shayne since she knowingly allowed his mother to be briefly imprisoned for the crime. Matt assured Dinah that she did the right thing and encouraged her to go through with the wedding. Though a regretful Dinah tried to tell Shayne the truth, Matt stopped her and later called her a hero for protecting the baby. Meanwhile, a lonely Matt failed at numerous attempts to flirt with the women of Springfield. Finally, he decided to sign up for an on-line dating service and talked Frank and Rick into the idea as well. Things got even more depressing for Matt when Vanessa married Billy again. However, the future finally started to look brighter when Maureen set Matt up with her teacher, Charlotte Jackson.