Dear Annie: Seven years ago, I met a guy on a dating site. I’m 13 years older than him, but I look much younger than my age. After we matched, he asked me on a date, and we kissed. From there, we kept texting, flirting and engaging in a lot of suggestive conversations — but he never asked me out again.
Over the years, we’ve remained close friends. He goes through periods where he stops texting me for weeks but always comes back. Despite this inconsistency, he’s helped me out several times — like giving me a ride from the airport, spending a day helping me clean my garage and assembling a bike for me. Each time, we end up kissing. The last time, when things started heating up, he pulled away, said he was sweaty and left.
We’re like best friends. He continues to flirt with me and often says, “Maybe one day we’ll be intimate.” From what he tells me, I don’t think he’s dating anyone. But after all these years, I’m starting to wonder if this is going anywhere or if I’m wasting my time.
Should I hold on to the hope that something romantic will develop, or is it time to give up and move on?
-- In Limbo
Dear Limbo: It sounds like you’ve been in emotional limbo with this man for years. While he values you enough to stay in your life and help out, his inconsistency and hesitation suggest he’s not ready or willing to commit to something deeper.
Ask yourself: Is this relationship giving you what you want? If not, it’s time to have an honest conversation with him. Tell him how you feel and ask what he truly wants. Be clear about your own needs -- whether it’s a relationship or closure.
You deserve someone who’s certain about you and ready to commit. Don’t settle for “maybe one day” when you could have something real with someone else.
Dear Annie: I recently read your column about a 47-year-old woman who had been with her boyfriend for six years and was eager for him to propose. Why do you think the advice to give him an ultimatum is the best approach?
In an era of equality, open communication and mutual respect, why should proposals be seen as something only men do? Why not encourage women to propose to the partners they love instead?
Doesn’t giving an ultimatum seem controlling or potentially codependent -- an attempt to force someone’s hand? Wouldn’t it be more empowering, loving and honest to suggest that women take the initiative themselves? And doesn’t it seem a bit outdated, or even sexist, to imply proposals are solely a man’s responsibility?
As a 40-year-old divorced man, I hope to find love again someday. If the woman I love is ready before I am, wouldn’t it make sense for her to propose to me? Why should we limit who can take that step?
-- A Different Perspective
Dear Different: Thank you for your letter filled with thought-provoking questions. You are absolutely right. Women can propose if they want to.