Dear Annie: Do I give romance another chance with an old friend?

Dear Annie: I’ve recently reconnected with a former co-worker with whom I had lost track of after her first husband committed suicide. She divorced her second husband when she found him in bed with another woman. She has an adult son from her second marriage.

After reconnecting, we’ve been talking three or four nights a week and finally agreed to go out to dinner with one of her new co-workers and her husband. When we met the other couple at the restaurant, my former co-worker latched on to my hand as she introduced me. As we were walking to my truck to go home, she latched on to my hand again and squeezed it hard enough to get me to stop walking. As I looked at her, she said for as long as we have known each other, she’s always wanted to hold my hand and kiss me, and she promptly kissed me on the cheek.

On our drive back to her apartment, she held my hand the entire way while we chatted about different things. She asked me what was wrong, and I said nothing, just that I was thinking about why she wanted to hold my hand and then surprise me by kissing me. We both agreed that cooking for one really stinks and that we both could use that other “special person” at this point in our lives. We both also agreed that, at this point in our lives, we both need some romance.

As we got to her apartment building, she gave me one more hug and kiss on the cheek and invited me in for one beer before I left for home. I accepted. Shortly after bringing the beers, she began playfully tickling me and I did the same, and that led to some serious kissing.

When we finally stopped kissing, I looked at my watch and said I had to go. I told her I had promised a friend I’d ride with him to Lynchburg, Virginia, to deliver some boxes to his daughter who had just moved into a new apartment and I had to be ready to go hit the road when he came to get me at 7:00 a.m. I told her that I had a good time and thanked her for getting me out of the house for something else other than work. We kissed goodnight, and off I went to get some sleep at home.

We tried dating 40 years ago and it didn’t click. My question to you is, do I give romance another chance with this woman?

-- Pondering

Dear Pondering: It sounds like you and this woman have a lot in common, not to mention chemistry. Have an honest, open conversation with her about what taking the next step looks like, and make sure you two are on the same page. You’re both single and looking for your next meaningful, long-lasting relationship -- what’s the harm in giving it another go? This could be the start of something beautiful.

Annie Lane

Annie Lane offers common-sense solutions to everyday problems. She's firm, funny and sympathetic, echoing the style of her biggest inspiration, Ann Landers. She lives outside Manhattan with her husband, two kids and two dogs. When not writing, she devotes her time to play dates and Play-Doh. Write her: