Jess is lonely and wants to have a boyfriend. Connie, Laila and Jess sign up for the new online dating site for their area. But she go no matches. Everyone thinks that she and Will would make a great couple but she doesn't. She thinks that Will is judging her. Jess thinks that she is not worthy of love, because her parents separated when she was little. Her mother left home and her dad worked away from home. Jess was only 7.
Will is being patient with her. Can he convince her?
I really liked this story. I felt bad for Jess. She has such low self-esteem. Will is good for her. I loved the secondary story line of Thomas and Connie. But I don't understand why they made such a big deal of the 10 year age difference. It's different when you are over 40.
Jess O'Brien has overcome a lotthe challenges of attention deficit disorder, the near bankruptcy of her beloved Inn at Eagle Point and her self-perception as a screwup in a family of overachievers. Now she's ready to share the future with a man. Her friends persuade her to join a dating servicebut she gets no takers! Which is fine with her childhood friend, psychologist Will Lincoln, who's already chosen the perfect man for Jess: himself.
Will has loved Jess practically forever. He knows her faults and her strengths. But for all Will's sincerity and charm, Jess fears he views her as some psychological case study. With her family and the town of Chesapeake Shores behind him, Will finally makes his case. But is it enough to convince Jess to take the risk of a lifetime?
"I have an idea," Laila Riley announced when she and Connie Collins turned up in Jess O'Brien's office at The Inn at Eagle Point on a Saturday night.
There was a twinkle in her eye that immediately made Jess nervous about what her friends had in mind. "Is it going to get us arrested?" she inquired suspiciously. Not that she was unwilling to take the risk, but she would like to know about the possibility in advance, calculate the odds and have a backup plan.
Laila grinned. "If there were anyone interesting working for the sheriff's department, we'd consider it, but no. This is just doing something outside the box, something none of us would ever consider unless we all decided to do it together."
"Do I dare ask?" Jess wondered.
"Online dating," Connie revealed. The lack of enthusiasm in her voice suggested that this had been Laila's idea and that Connie had only agreed because of the same boredom that had been affecting Jess's mood recently.
Jess, however, wasn't quite that desperate. "You can't be serious."
"Oh, but we are," Laila confirmed.
Jess studied the two women who'd invaded her office on a night of the week when most attractive, intelligent women should have been out on dates. Connie and Laila were related to her indirectly by the marriages of their siblings to hers. They were friends by choice despite the differences in their ages.
Connie was the forty-one-year-old single mother of a teen who'd recently left for college. Her younger brother, Jake, was married to Jess's sister, Bree. Laila was the thirty-six-year-old manager of the local bank and younger sister of Trace, who was married to Abby, Jess's oldest sister. Jess, at thirty, was the youngest. At times it seemed as if everyone in Chesapeake Shores was related to an O'Brien one way or another.
"Okay, now, let's think about this," Laila said, making herself at home by pouring a glass of tea from the ever-present pitcher on Jess's desk. "What are you doing tonight? I mean, seriously, here you are in your office when you should be out on the town, right?"
Jess glanced at the ever-present mound of paperwork on her desk. It was the worst part of her job. She was beginning to see Laila's point.
"And does that make one bit of sense to you?" Laila pressed. "What is wrong with the men in this town that the three of us are alone on a Saturday night? We obviously need to broaden our horizons. Put ourselves out there. Stir things up."
"And find some geographically unsuitable men who'll never be around?" Jess replied. "Seems counterproductive to me."
"I thought the same thing at first," Connie said, beckoning for her own glass of tea. Laila poured it and handed it to her. "But the sad truth is that boredom has made me more open-minded. For the longest time I couldn't wait until my daughter was grown and off to college, but now that Jenny's actually gone, the house feels so empty I can hardly stand it."
"And I've been mind-numbingly bored ever since Dave and I broke up three years ago, which is saying something, since dating him was about as stimulating as watching grass grow," Laila said. She sat up straighter. "Online dating is the perfect way to change the status quo. It's trendy. It'll be fun."
Jess remained unconvinced. She turned to Connie, who was known for being sensible. "Are you really in favor of this?"
Connie shrugged. "I can see some advantages."
"Geographically undesirable," Jess repeated with emphasis.
"Not a problem," Laila insisted. "It's a new local service. These men are all right around here."
Jess couldn't quite wrap her mind around either the idea or the fact that Connie was willing, if not eager, to try online dating. Looking her in the eye, Jess began, "But I thought…" Her voice trailed off. She wasn't supposed to know that sparks had been flying between Connie and Jess's uncle, Thomas O'Brien. Her brothers Connor and Kevin both had sworn her to secrecy. She sighed. "Never mind."
Connie studied her with suspicion, but since it was a kettle of fish she clearly didn't want to dive into, she remained silent.
Laila, seemingly unaware of the undercurrents, jumped back in. "It's perfect, don't you think?" she asked excitedly.
"Are there any single men around here we don't already know?" Jess asked, still skeptical. "Isn't that precisely why we're sitting here on a weekend without dates?"
"The region does extend beyond the town limits," Connie conceded.
"It includes Annapolis," Laila explained, pulling a brochure from her pocket and handing it to Jess. "See, Lunch by the Bay. Doesn't that sound lovely? And that's all we'd be committing to, an occasional lunch with someone new. It has to beat waiting around to be noticed in the bar at Brady's. If I spend any more time in there, Dillon's threatened to name a barstool after me."
"At least you'd have a lasting legacy of your life in Chesapeake Shores," Jess teased. "Much better than having your picture on the wall of that stodgy old bank your family owns and that you're so attached to."
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