Understanding Men: How to Handle a Vague Date Request


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Here’s a scenario almost every single woman has run into dating over 50 or at any age really.

You meet a cute guy at work, in a store, at a bar, at speed dating, etc. You chat a bit and he seems interested. Then he takes the next step and asks for your number, saying you should go out for coffee or dinner sometime. You think to yourself, “Hey, he asked for my number and asked me out. He must be really interested in me!”

Maybe he texts you and starts a conversation. He might even ask what you are doing over the weekend. You think, “He’s asking if I plans for the weekend. That’s a good sign!” You start feeling excited about the possibility.

But somehow, you never actually connect in person and the date doesn’t materialize which turns out to be a major bummer!

What the Heck Happened?

Women ask me this very same question all the time because this sort of thing is so incredibly common. The trouble is there are clues, but many women don’t pick up on them. You attach meaning to interactions that don’t really have meaning and then you feel hurt and terribly disappointed.

I understand – I’ve been in your shoes. And I learned everything the hard way through the pain of experience. That’s why I want to open your eyes now and share with you these insights to help you with understanding men.

Learn to Read Between the Lines

When a man asks for your number and says,  “Let’s go to dinner sometime,” could mean a few different things. He may be:

  1. Testing the water to see if you are interested
  2. On a mission to collect women’s phone numbers and boost his ego
  3. Interested, but unsure of himself
  4. Interested, but minimizing the risk of rejection

However, no matter what the reason, this is a “lame” request and shows a lack of masculine leadership. Now that’s not always a terrible thing. But it clearly can be annoying as it leaves you left wondering and often dangling in the wind. When a man asks you to go out sometime, it’s more like he’s fishing or tossing out some bait versus asking you out.

What YOU Can Do

To alleviate some of the stress, I recommend you respond like this next time a man asks you out without any specifics, “I’d love to! When were you thinking?”

This will help cut through the nonsense. Either he’ll pick a day right away or stutter and do his very best to weasel out of it. Your quick response puts him on alert and will clear up the mystery. How he responds tells you everything right then and there, speeding up the process.

Another Option

Some women won’t feel comfortable taking such a direct approach. If that sounds like you, the next best thing is to EXPECT his lack of follow through so you won’t be disappointed later when he never sets a real date up.

Don’t Make Excuses for Him

But, whatever you do, DO NOT ask him out. To help you with understanding men, this is like doing his job for him. If he’s not committed to asking you out, is that really a man you want to date?

The Shy Guy

Forget all that shy guy stuff you might be toying with. That’s just making excuses for his wimpy behavior. If you don’t want to always be taking the lead with a guy, don’t start doing so from the very beginning. Shy men know what to do to go on a date with you and they will do what it takes when they really want to see you.

The Intimidation Factor

Don’t believe that nonsense about how you intimidate men either. If you are intimating, cut that out and learn to flirt, be warm and friendly. Your intimidation factor is not a reason to taking the lead. I have found women who ask men out are the first to complain they are doing all the work in the relationship. You set up your relationship from the very first conversation. So if you don’t want to run everything, hold back off on taking charge.


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, MSN.com, MORE.com, Connecticut Magazine among others around the world. An established author, you can find her 6 books on Amazon.

11 thoughts on “Understanding Men: How to Handle a Vague Date Request”

  1. Hi Ronnie,

    I have met this guy, several times, for a couple of dates. We happened to be in his country when we met (I was studying and he was local) and just so happened that he relocated to my home country and I was coming back. The first two dates were fine and he wanted to see more of me. Then after the third date, he said he just didn’t feel it. I moved on, came back home and we kept in touch here and there. He arrived one week later to my country and I helped him move, showed him the local places, etc. He was all of a sudden very responsive to me (through whatsapp), which he never really was before. Tonight, we were supposed to meet up for a drink, but he didn’t tell me where, so I called it off and told him that in future he needs to give me details. He said “why do things have to be so complicated with you?” Is he using me just because he is in this a foreign country with no friends? What should I do? Thanks! Rachel

    • Hi Rachel, Yes, I think he’s using you because he doesn’t know anyone else. Why help a man who said “he doesn’t feel it” about you? Who needs a friend or date like that? This is an opportunity to value yourself and walk away from anyone who treats you this way. Asking for date details is certainly reasonable. However, rather than try to change a man by telling him you need details, ignore him and move on. He doesn’t even appreciate the help you provided. There are better men out there.

  2. Hi Ronnie,
    So this guys who works down the street keep telling me that i look great whenever I’m in a new dress etc. When we talk like maybe 2-5 minutes when hes passing by etc. He says he will cook me a meal at his place sometime. responded that that would be lovely. so the other day we were both working around 10hr shifts and h comes over and says would u like to have a few drinks later tonight. I said ya sure. Then at the end of my work day ( 8pm) he comes over again and says hes just heading home to shower and will give me a call. so i went home too and got ready to go out. Then when I’m home getting dolled up i get a text asking if id eaten dinner…I’m so confused can u let me know whats going on in his mind

  3. Hi Ronnie,
    So I met this guy at work and we were pretty good friends throughout the five months we worked together. When he left, I asked it everything was okay and he explained how the reason he left was he was going through a bad time with his parents and such, but that was a few weeks after he left in order to sort himself and his life out.

    Then not too long ago, out of the blue he started messaging me again and asked me put on a date in which I said yes to.

    We still haven’t been on the date and that was a few weeks ago, but he said he’s still up for it whatever it may be and because I’m not exactly a local in my place of work I texted him on Saturday asking if he was out as me and my friends went out to a nightclub where he often frequents. When he realised I had went out, and he hadn’t he seemed so bummed and we got talking again.

    Then the other day I asked him if he was busy over messenger and he still hasn’t read or replied.

    What do I do now?

    • Hi Amber, Do nothing. stop doing his job. He knows how to reach you and he knows how to go on a date. His lack of planning and initiative show you he’s not ready. Some guys like to text and talk even though not ready to date – it provides fun and contact with no downside or expectations. Just pull back and go meet new men who are looking for a relationship. He’s not the one.

  4. Hi Faye – there’s no explaining the crazy stuff people do. If you need to know why, you’ll drive yourself crazy because the truth is you will NEVER know. Let it go with grace and move on.

  5. Ronnie I had been wanting to go out with this guy and its almost as if this guy knew I wanted to go out with him. Do you think he knew I wanted to go out with him? He sure did make me feel like a fool.

  6. But the first date went ok. He set it up with me and there weren’t any games. I would have thought that if he played games with me on the second date there would not have been a first date. Why did he go through with the first date?

  7. Hi Ronnie,
    I have went out with this guy before. We have been texting some over the past 2 weeks. He asked me if I was ready for a date and I told him yeah whenever he was. He then said that he wanted to go to this restaurant and he told me to pick the time and I asked if the coming up Friday was ok and he didn’t answer and he started talking about somethingelse. So I asked him again if Friday was ok and he still didn’t say yes or no. This guy asked me for a date and then didn’t answer me when I asked him if Friday was ok (and he told me to pick the time). What is going on here? Did this guy ask me out to try to play a game on me by doing me this way? Im so embarrassed because now I agreed to go out on a date with him but he didn’t say yes or no when I told him a day.What is going on here?

    • Hi Faye,
      What is going on? He’s playing with your head. (Some women do this to men as well.) Stop texting and hoping he’ll come around and be a gentleman (he can’t) and move on. In the future, when a man asks you to pick a date, then doesn’t respond, stop texting right then. Don’t follow up with men who don’t show you the respect you deserve.

      There’s no need to be embarrassed in front of him – he’s an idiot to play these games. Don’t give your power away to him by feeling badly about this. Just get out there and meet some new men – you’ll find better men out there for sure. Establish standards for how you expect to be treated and accept nothing less. Put up with no shenanigans. A woman who holds herself in high esteem is treated well.

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