Dinner With Cupid

Reality rerun

Will a TV 'bachelorette' finally get her rose?

March 20, 2011

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Kerri Oliveira, 32, recruiting manager

What makes her a catch? I’m willing to take chances to find the right guy – I was on season 3 of The Bachelor.

Describe your perfect mate: He’d look like Javier Bardem and would be a veterinarian.

Jeff Kaplan, 31, accounts manager

What’s the last thing you read and enjoyed? Hard Sell: The Evolution of a Viagra Salesman

What would your exes agree drove them nuts about you? My honesty and bluntness

5 p.m. Solea Restaurant & Tapas Bar, Waltham

Sneak preview

Kerri: I felt completely calm but intrigued. I had no idea what to expect.

Jeff: I went in with no crazy expectations. If it went well, great; if it didn’t, I’d have a lot of stories to tell Globe readers.

Kerri: We arrived at exactly the same time. I saw him walking into the restaurant and asked if his name was Jeff.

Jeff: I had a gut feeling it was her. She was very attractive, with a great smile and dark hair. I was pleasantly surprised.

Kerri: [He] presented himself well. Neatly dressed, which is always a plus.


Jeff: We got a variety of food, as it was a tapas-style restaurant. I’m not a picky eater, and we agreed on what to order.

Kerri: I had been there before, so I took the lead.

Jeff: I heard a lot about the love of her life: Parker, her dog.

Kerri: He was unfortunately bitten by one recently but still loves them! A true dog lover! We also talked about real estate, as he owns and I am looking to buy.

Jeff: I bought my condo about four years prior, and I gave her some advice on the good, bad, and ugly of what I went through as a first-time home buyer.

Kerri: We talked a lot about our careers, how priorities have changed as we are getting older. He recently switched jobs so that he has a better work-life balance to potentially dedicate to a relationship.

Jeff: She has lived in LA, NYC, and Boston and has a lot going on with her new job.

Kerri: He is a little younger than I am. Not a complete deal breaker, but I am looking for someone older and therefore more ready to settle down.

Jeff: I’m not sure if being younger was a bad thing, but she seemed a little caught off guard by that. Age is just a number, so it didn’t bother me.

Closing credits

Kerri: I knew instantly this wasn’t a love connection. You just know when it’s there and when it’s not.

Jeff: I was getting the “friendship” vibe from her, which was totally fine. She was attractive, but it would have been better if she relaxed and laughed a little more.

Kerri: I felt like I did most of the question asking. I typically like someone who takes the initiative in getting to know me.

Jeff: I felt like she was just going through the motions. Kerri let loose after she had a few drinks, which helped. She wanted to leave sooner than I would have, but I wasn’t going to force it.

Kerri: We had spent two hours over dinner; it was time to go.

Jeff: We did the “hug it out” thing, which was fine. I said I’d be willing to hang out again, but she basically walked off saying “maybe.”


Kerri: B-

Jeff: B

Second date?

Kerri: Nice guy with great potential but just not for me.

Jeff: We didn’t exchange numbers, so I guess it’s a no.

Go on a blind date We’ll pick up the tab. Fill out an application at

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