He emails and texts…and emails and texts. That’s it. The phone isn’t ringing and he’s not asking you out. All you want is for him to plan a freaking date so you can actually spend time together! How do you get him to do that?
It’s important that you know, not just how to ask for what you want, but that it’s important to do so! Keep reading for the story of Debbie and Bill. It’s a perfect example of how and why you should kindly let a man know what would make you happy, and give him the chance to do it.
Hi B.,
We seem to have a lot of interests, needs, and beliefs in common, which is really cool. And you’re pretty damn handsome. 🙂 I guess I’m too old, and quite clear about what I eventually want…that I want you to know what I’m thinking. It would be great to see you again. If you are interested in getting to know each other better, you have my number; would love you to call me. Let’s have a fun lunch or dinner together.
Enjoy your day!
D.
Bill calls Debbie within a couple hours, and asks her out to a nice dinner for the next Friday night.
Debbie has shifted the dynamic of their relationship. How this will end is yet to unfold, but here’s the point: She (like you) is a mature woman dating to find love. Respect yourself enough to ask to be treated special and seriously; especially after a few encounters with a man.
If a man you’re interested in isn’t treating you this way, tell him what you like about him, and then kindly let him know what you want or need. By telling him clearly, you’re giving him the chance to do it. If he responds positively, that’s good! It shows he cares for you and wants to make you happy. If he doesn’t step up, it just means he’s not a good match for you. Accept it and move on. Next!
P.S.: Great work, Debbie!!! I know it was difficult for you…but you rocked it!


Bobbi Palmer says:
KB, what you describe sounds more like friends with benefits than a real relationship. The time to communicate what you are looking for and your relationship goals is BEFORE having sex. Usually the dating part comes first – dinner, hikes, coffee, movies – then, if all goes well and you are both on the same page – then intimacy. If you want something more than a booty call with this man, it’s time to put a break on the sex and let him know your true feelings and relationship goals. Otherwise, if you want a real relationship, you are wasting your time. It may be too late. Maybe not. – Bp
KB says:
I know this is an old post, but I’ve been reading through the blog so I hope someone is stil out there reading comments because I need help.
I met a man at work (we are colleagues but not at all interdependent on each others role; we don’t share office space or see each other daily at work).
At our first introduction it was clear we were attracted. Later that week there was a professional cocktail party that we both attended and he was very attentive. I gave him a ride home, he invited me in, we talked and shared a beer, but nothing happened (neither of us made a move). The day after, I sent a txt saying I enjoyed the evening. Since then we have communicated by text, and he drops in my office to say a brief hello (which I adore).
We always meet at his place and had sex on the 4th or 5th meeting. Since then it’s always been meeting at his place, having sex, then chatting or sharing videos. He’s not much of a talker (but I think it’s partly cultural -he’s not American).
We’ve been “seeing” each other for about 6wks. This week we started talking about going hiking.
I cant get a read on him at all!
We are both midlife. He’s divorced, no children. Should I just wait and see how the hike goes? I’m definitely one to enter cautiously, but I really enjoy his presence and would like to know where we stand. any feedback is appreciated!
Bobbi Palmer says:
Hi A. Yes, I do agree that when a man doesn’t step up at the beginning he most likely won’t as time goes on. Just need to remember that with more mature, confident, accomplished men they are a little different. They will definitely want to show up and step up if they are interested, but they also need something back. They won’t chase. So we should also show them, even early on, that we are interested and also willing to give. Believe me, there are a lot of women out there just looking to be taken care of while giving nothing back. (It’s not just us women that experience the users!) So I”m saying that even on the third or so date, let him know by giving something – offering to buy coffee, the movie, bringing him a little flower from our garden. Alot of men will turn down your offers of paying, but you’ll be letting them know that you’re not one of those takers. And you are SO welcome! Thanks for letting me know that my work is helping you. I really do love to hear that! Hugs. Bp
A says:
Hi Bobbi,
I’m interested in your take on Bruno Rivard’s comment.
Personally I strongly disagree. Women naturally are caregivers and planners. Men often need to develop those skills as they mature and become more mindful. If he doesn’t have them, he’s not MY relationship material.
If a man doesn’t take the initiative early in the relationship, and step up in showing he is a provider, in my experience they typically flake later or never step up as equal participants….& often are takers. After settling into a real relationship, I can see being more involved together making plans and splitting costs, but not initially.
Your thoughts?
Thanks for all that you do!!!
Bobbi Palmer says:
Thanks Sum Guy. We like hearing from you. I do agree that if he’s not asking, you can definitely go for it. Though I don’t suggest a woman do that until after she tries to show him clear interest. Yes, it’s a bit old-fashioned, but after years of coaching and also talking to men, my “data” shows that things still work better when the man takes the lead. Most often when I see the woman do it, the man turns out to be someone who is not very serious about putting work into developing a relationship. Bp
Sum Guy says:
There is a simple answer, ask him out yourself.
Unless you are caught up in traditional gender roles (or want a man who is) guys love women who show interest in them by asking them out. It shows confidence, which is sexy in women as well.
I like Debbie’s reply but Bill seems like a total flake.
Bobbi Palmer says:
HI Leslie, Nope, not going to tell you to reach out. I’m going to tell you to move on! There are so many reasons why he hasn’t responded; most having nothing to do with you. You have no idea what’s going on, but you DO know all you need to know: he’s not responding. So…live your life. Reach out to other men. Get out and have some fun…hopefully where there are single men around. Have fun! Hugs, Bp
Leslie says:
I am getting on line after being in two committed relationships after my divorce. I was on-line once about 14 years ago so I don’t have a ton of experience and it has changed a lot since then.
What does one do when a guy has winked at you, and you wink back in interest and then……nothing!? Its been almost 2 weeks, so this isn’t me being impatient. Shouldn’t my “wink” be perceived as a “green light” to proceed with him getting in touch?
I have a feeling I know what is coming….the suggestion for me to reach out. But I am wary of having to do “all the work” here since I clearly let him know I was interested. Can you provide some guidelines to approach in this example – where they have indicated interest first, you reciprocate and then….nothing?
Are Texting and Dating a Recipe for Relationship Disaster? – Online Date Tips says:
[…] Honestly, half the time I don’t know what a guy means based on twelve words on a screen. And even if I think I know, I’m loathe to guess. Instead, I recommend that she invites him to call her in a kind and open way. […]
Bruno Rivard says:
As a 40 year old man I would give the following advice, particularly if looking to date educated and smart men: 1. It’s okay to be keen and interested but don’t rush into getting all serious and ominous. the idea is to get to know him, not grill into a crisp. 2. This is really serious: Get into the habit and mind frame of asking the man out on a date and partake together in planning it. Do not expect him to plan the date alone, though he might still do that. Plan stuff yourself, at about the same rate he does, as it comes. Typically a man in his 40s, or mature men in general may judge you negatively if you idle out while still interacting, when it’s obvious you are waiting to be asked out and are avoiding participating in planning activities. It may give the impression that you are difficult, bratty, and selfish. This is the #1 reason I or many other men write a woman off as relationship material. 3. Have your own mind and opinions, don’t pretend to agree with everything he says just to be pleasant. 4. Be excellent. Know your stuff and provoke him into discussion and debate. Expect to be challenged back and demonstrate how smart you are. Smart men absolutely adore women who do this! 5. Avoid giving the impression you might be a golddigger or have to be made to feel ‘special’ continually.. Unless you are looking like a 25 yo model this will cripple your relationship prospects. Go dutch on everything. A good man how cares will do all sorts of things to please you, and you should reciprocate. A constant need to be made to feel ‘special’ betrays self-esteem issues and immaturity. It’s a sign that you will be a bad investment. Best of luck!!
Bobbi Palmer says:
Welp, Lorraine, then Debbie should just move on. She did her part, and if he’s not responding with clear interest…Next! 🙂 Bp
Lorraine says:
I love the way Debbie changed the dynamics in her email to Bill.
What if Debbie had sent that email and he never replied to it at all……. or he did reply with a very short response with something like…Yes it’s nice to hear from you too and .I’m sure our paths will cross again.
Or better yet……Things have been very busy at work and we can catch up when things slow down for me.
How should she respond to that?
Allyson says:
I love the advice for women to ask for what they want! I wouldn’t let “months” pass first, though. After a couple of weeks, I’d suggest doing an activity based on on of our common interests, If he wants to go out with me, we’ll make the plans. If he wants a rain check due to schedule issues, I’ll agree — once. If rescheduling becomes a thing, I know I’ve got a flaker/fader on my hands or a man who’s just not that interested.
” By telling him clearly, you’re giving him the chance to do it. If he responds positively, that’s good! It shows he cares for you and wants to make you happy. If he doesn’t step up, it just means he’s not a good match for you. Accept it and move on. Next!”
Yes, this!!
Bobbi Palmer says:
That sounds so harsh, Noquay. Seeing him getting back to his old ways is merely an assumption. Maybe the past guys did that, but this guy won’t. After a few emails or even one date a man doesn’t know you very well yet; he’s not courting you. Having realistic expectations – aka giving a man a freaking break – is something I highly recommend. These guys aren’t auditioning for you, nor are they taking some test. They are just human like you. I support giving a guy some encouragement and a chance to be his best self. If he doesn’t step up after that…then move on.
Noquay says:
This kinda scares me Bobbi. The only time this dude took this woman out on a real date was when he was pretty much confronted. I can see him getting back to his old ways again. If someone cannot maintain real communication with me, can’t be bothered to truly date me, they’re gone. You’re either in it or you’re not.