Dating after Divorce: Why Doesn’t He Ask Me Out?

Dear Dating Coach,

I’ve been divorced for 4 yrs and now I’ve become interested in a guy I work with. My friends tell me he likes me a lot and he lost his wife about 4 yrs ago. I’m very old fashion and wasn’t brought up to ask a guy out. He comes to visit my office every day, about 2 to 3 times. I think he is just as nervous to ask as I am.

I really like this guy. Sometimes we talk for hours and we have both worked together for a long time. But no one is making a move to ask the other out.  Being old fashioned i don’t want to make the first move, but I don’t want to lose a chance of happiness with this man. How can I break the ice without scaring him away?

Office Romance

Dear Office,

I’m glad to hear you are old fashioned – that is exactly what works best in dating! Things tend to work out better when the man asks the woman out. That said, this situation needs some clarifying.

Your guy got married once, so he does know what to do. All men know what to do no matter how shy they are. Why isn’t he asking you out? here are some possible reasons:

1. He’s not ready to date and still healing from losing his wife. This happens often for widowers – some men just take longer to recover than others. He may be still pining away and that means his heart might not be open fully to you and he’s not emotionally available.

2. He likes you but isn’t sure you are the one for him. He enjoys your companionship, yet doesn’t want to spoil the friendship to risk taking things to the next level.

3. He’s lacking testosterone to make the first move, which is not a good sign in my book. The last thing you want is a man who needs babying or hand holding. That might seem nurturing at first, filling the Florence Nightingale role. But it will get tiresome to have to take the lead all the time and make all the decisions.

4. He enjoys your company and his fulfilling his need for female company with you. But he’s not relationship ready. Lots of single men tend to do this. My friend and colleague, Katherin Scott, insists that her male dating coaching clients stop spending time with their female friends while searching for a romantic partner. Once they get their “fix,” they feel less motivated to do the work of looking for love.

However, all that said, if you really want to push the envelope here, try one of these suggestions:

1. Get your friends to suggest that he ask you out
2. If you start talking about a movie or new restaurant, say “Hey, why don’t we check it out?”
3. If he can help you with some project at home, as for his help. Say, “Do you have any time this weekend to come by and help me with that?”

Just remember, you can bring a horse to water, but you can’t make him drink. If he’s not ready, he might take you up on your offer, but still not follow up with his own.

Whatever you do, only make this move ONE TIME! If he really is as interested as your friends say, he will pick up the  ball and ask you out for a second date. And if he doesn’t, then please move on to find a man who is capable of asking you out and being in a relationship. You deserve to find love with a man who is emotionally available and ready.

Single for too long, Ronnie wanted to find love. So, she made a few tweaks and then dated 30 men in 15 months to meet her adorable husband Paul. Discovering the keys to midlife dating, she founded It’s Never Too Late for Love to help other smart, successful women find love too! Her mission is to share her proven dating advice  and keen insights about men with women everywhere who are serious about finding love with the right man. Ronnie Ann Ryan, MBA, CCC is a Certified Coach who has helped 1,000’s of midlife women with her Love & Dating Coach services. She’s been featured on BBC’s 5 Live Radio, NBC, ABC, and Fox News, NPR, eHarmony,,, Connecticut Magazine among others around the world. An established author, you can find her 6 books on Amazon.

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