Exactly What to Say to Men in Difficult Situations

In dating, knowing what to say to men, especially in challenging situations, is the key to attracting the right men. It’s also the key to developing and maintaining fulfilling relationships.

One of the most important ways I support my coaching clients is by helping them communicate well with men. Online or offline, good communication requires certain knowledge and skill. It’s a bit of an art, actually.

When challenging situations come up, I help women write a script that not only communicates effectively but also feels comfortable and true to who they are.

This week I helped “Kathy” tell the man she’s been out with four times that she’s not yet ready for intimacy. She was going to break it off with him, but I convinced her to try to tell him and see how it goes. He seemed like a great guy to me.

Kathy had that conversation (see our scripting below), and his response was, “Okay…I can do that. Thanks for telling me!” There you go. Not only did she avert ending a potentially lovely relationship, but she earned his respect and opened up the possibility of further meaningful conversation. Well done!

Here are some other things I’ve helped clients with this week:

Showing a man she is interested without being too pushy. (Remember: Showing interest and taking the lead are very different things!)
Apologizing and showing regret for something she said
Writing killer online dating emails that get read and get responses
Answering the question “Why haven’t you been married yet?” when she goes on dates (Ugh…I used to get that question all the time! Guys: there is a better way to ask this.)

Here are specific examples for some situations:

If you want to…

Show a guy you’re interested without being too pushy…

Instead of saying…

I’d like to go out. How about Sunday?

Say this…

I really enjoy talking with you. It would be great to do it again some time. (Make good eye contact…smile. Show him you mean it.)

If you want to…

Tell a man he is going too fast and you are not ready for intimacy…

Instead of saying…

You’re going too fast for me!

Say this…

I like you and I’m enjoying getting to know, Bob. And you ARE pretty hot. (Again, eye contact, smile.) I’ve found focusing on getting to know each other works best at first. I’d like to [fill in with how you would like to proceed]. How does that sound to you?

If you want to…

Write killer online dating emails that are getting read and getting responses…

Instead of saying…

Hi. I like your profile. I see we have many things in common. Read mine and write if you’re interested.

Say this…

Hi, Bob.I understand what you said about [thus-and-such], and I completely agree*. (Agreeing with a man is very complimentary.) In fact, [give him a real-life vignette that shows you have that in common]. There’s more to the story, and it’s pretty funny. [Create some intrigue and set up for future conversation.] It would be fun to learn more about [something he has in his profile]. Sounds cool. What was it like? [Or some direct question that’s easy for him to answer.]

I’m looking forward to hearing from you. [Show that confidence, girlfriend!] Enjoy your day.

When you connect with a guy, don’t do it on something intellectual. That’s not very sexy. Connect with some life event, feeling, dream, value, etc. For instance, if you went to the same college, great! Don’t just tell him that – it’s boring. Tell him how you used to connect multiple power cords so you could pull blenders out to the quad and host daiquiri parties. (Okay, I admit, that’s directly from MY life experience. But I think you get the point.)

If you want to…

Answer the question “Why haven’t you been married yet?”

Instead of saying…

It’s none of your business OR because I haven’t found the right guy yet…

Say this…

My life has been great but just hasn’t gone that way yet. But I’m ready and looking forward to when I meet that terrific guy I spend my life with.

It’s actually not so hard as we make it to be. Most men want to understand us, and they want to please us. They just want a little help!

This is no different than learning how to communicate with your boss or that passive-aggressive gal at work. You need to learn some basics, and then you need to practice.

Do you see the pattern in all these? When trying to address a potentially difficult situation:

Be positive
Be direct
Speak from the “I”
Don’t demand

Try these and tell me how it works for you! Leave me comments here or go to my Facebook Page and share your experience to help others.

These will also help you:

The Delightful Difference Between Dating Mature Men and Boys

Nancy January 23, 2016, 3:05 pm

Here’s a question: What do I say when a man I have not yet met asks me if I have any plans for retirement? The reality is, I have paid off my small house, have a kid in college, receive alimony, was under-employed during the recession and am now maxing out my work retirement plan . . . I have long-term care insurance at a reasonable price . . . I have a nest-egg and took one preparation for retirement class, but feel like it really depends since I will lose alimony if I live with someone (my ex added that to our marital settlement agreement and I had bigger fish to fry so let that go) . . . I want to be financially secure but I haven’t had a windfall that would easily ensure I would be comfortable retiring early, and none are in store.

I want to convey that I am not opposed to retiring early if my financial future looked secure, sort of “never say never” — without feeling put on the spot and like I need to start angling to find out if he is offering a “two can live as cheaply as one” potential scenario, which, if we wanted to be together anyway, would ease the way.

I was really happy to land a permanent job again in my field over age 50 and believe in taking care of myself and not “betting on the prince” while at the same time have never felt super-ambitious about work, and my job is semi-fulfilling but still more of a “work to live” option for me instead of “live to work”.

I don’t have a simple, warm, receptive, and open-ended answer in my back pocket when a potential date (for instance, this one who invested money early and retired at 50) wants to screen me for my likelihood of being footloose and fancy-free in the foreseeable future.

The second (related) question is, two men this year were angling for me to make a date during a weekday . . . because they live about an hour away and I indicated I telecommute four days a week — which to me means I can work wherever there is an Internet connection, if a relationship were to ensue.

My work takes special concentration and I am on daily deadline. I am salaried and have some flexibility but the employee handbook does specify working 8:30 – 5:30. It would not be fun for me to meet during the workday and have my pressures looming over my head during the date.

Plus it is a bit of a turn-off to have an option that would not be pleasant for me proposed — even though I understand they want to not be on the freeway when it is congested. (One guy wanted to meet on a specific morning, the other wanted to meet halfway for lunch, which sounded like a 3-hour time commitment to me.)

How do I frame the geographic availability issue so that my work day is respected, while, if possible, also indicating geography may not be a major hurdle in a committed relationship because I am someone who could visit back and forth pretty easily if we became exclusive romantic partners? I don’t think they are really hearing the second part, and maybe I am complicating the message by wishing they could see the possibilities further ahead. Maybe guys are just thinking of immediate solutions and the near-future of becoming acquainted in person.

Thanks!

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- Bobbi Palmer January 28, 2016, 1:50 pm
  
  Hi Nancy. There’s lots of future-thinking going on with everyone. With the financial question, it’s pretty idiotic of the guy to ask you that before you even meet. He needs a dating coach. 🙂 That said, I would just tell him that you are quite secure, take care of yourself financially and have made plans for your future. That’s all he needs to know. I get a guy doesn’t want someone who is looking for a sugar daddy, but c’mon? Who asks that before he even meets? Anyway, if he wants more than that, I’d say ‘thanks but not thanks’ to meeting him.
  To the 2nd question, it’s really more than I can answer here, but if you definitely don’t want to meet during the day, tell them the truth. Let them know that, while you work at home, you honor your commitment to your employer to work certain hours. Though I can’t see why you couldn’t take a long lunch to meet a nice guy here and there. You know best, but sounds a bit inflexible to me too. Glad you’re here! Bp
  
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Shearies August 28, 2014, 12:24 pm

Hi Bobbi, I’ve been talking with this man for the past year, He has said to me that he has been watching me for awhile now. He helps his friend with his merchandise on the street vending everyday and there have been times when he’s not there or when he goes away. I see him everyday on my way to work only because I take the bus that stops right at the spot where he is during the day. So for the past year we’ve been talking, He would text me sometimes or call sometime. Though I don’t worry myself with that if he doesn’t text or call. I know that men get busy or maybe it could be something else I don’t know. This past summer we’ve gotten a little closer to just hugs and kisses (just pecks on the cheek) very few on the lips. He always tells me how I look and I tell him too, though he’s only in his (as he calls it) jeans/slacks and t-shirt, sneakers dirt clothes. I do dress classy/fashionable most of the time and then there are those times when I dress down somewhat but a classy dressdown. He hasn’t asked me out on a date, though he has told me that he’s trying to pay for his new car that he just brought ( I haven’t seen it). We haven’t been on any dates. He’s late forties and I’m early fifties, but he said that doesn’t matter to him, and he still talks to me and gives me hugs. At one point I went on vacation for about a week and didn’t tell him. But when I was back to work he saw me and gave me a strong hug and he kissed me on the cheek and wondered where I was I told him I was away. As we were talking about my trip he grabbed me around my waist and pulled me toward him and I smiled. I liked it though I didn’t know what to say. But my concern is that I want to tell him how I feel and how it is frustrating me as to how he feels about me. I want to ask him and want to share my feelings because if he’s not into me then I don’t want to fool myself. He always say’s he’s going to call me but he doesn’t I just say ‘ok’ and I don’t call him either. I don’ t know what to do to not push him even though he has said to me that he’s just taking his time with me. HELP.

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hannah April 29, 2014, 8:56 am

It’s funny, all my problems with men come from expecting them to take care of me! What surprise they take care of themselves instead and I have to be a grown up too!

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- Bobbi Palmer April 29, 2014, 10:10 am
  
  Yep, you got it Hannah. Hahaha! Welcome to to the world of grownup dating. It’s really a great place to hang out. Much more fun than that silly stuff we did as younger women. And the men are so much nicer to be with too. All kidding aside, it’s new perspectives like this that make ALL the difference in your experience. Let me know how it goes. Hugs, Bp
  
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- Bobbi Palmer May 4, 2014, 10:11 pm
  
  You’ve got it Hannah! it’s the grownup thing. 🙂 Bp
  
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Sam March 31, 2014, 11:14 am

Hi Bobby,

I am dating this guy its been a month. He is nice and caring. Our first lunch date rolled on to cinema too. Then we were supposed to have a 2nd date next weekend, and he got caught up with some task. He texted sorry like million times and asked me not to get mad. So he also told me he will make it up to me and invited me to his place and said he will cook for me.. He cant cook at all. still.. So I went to his place next weekend. it was nice, his brother and a frnd was there. we watched films got along with his brother and we came bit closer. He was supposed to be travelling for 16 days.. So, next he asked me to go to his place after i finish my work. He was free. I went and we got really close watched loads of films and ended up in bed. It was awesome.. It was too long for me that i had it. He said for him too. He was so shy, he was even telling me sorry babe im so nervous. It was a perfect night. The night before he was travelling he finished work around night and insisted to see me and asked me to go to his place. As he really wanted to meet me before he leaves. I went and I stayed. But yesterday i saw a picture of him in instagram with a girl. with hash tag “love” posted 5 weeks back. which means a week back before we started dating. I checked the grls profile, she had hashtag “boyfriend”. Important to mention, just after our first date, he called me wen i was in a meeting. later i called him back he didnt pick up. After 10/15 mins i got a blank call. When I saved the number i saw it was a grls number. It is the same girl from instagram. I asked him that day, he said she is a friend. And yesterday when i saw the instagram photo i asked him straight. he said again she is a friend and when he comes back he will throw a get together so that i can meet her. But this thing is killing me. I dont sleep around, and my last relationship was a year and half back. I didnt date anyone in between as i didnt feel like. Now i already slept with this guy trusting him. Is he really double timing? i tried to check all insta photos and found he knows this girl been a year. And the girl is also added with his brother and friends profiles. whereas he hasnt added me on any of them yet. Although i met his brother and friend. I really dont know how to deal with it. this is killing me. I don know what to believe. the girl clearly wrote bf and posted the pic 5 weeks back. please help!!

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Suzi August 22, 2013, 9:41 am

If only I’d had your help years ago I could have transformed myself into a softer more vulnerable Calamity Jane and found happiness and love years ago. Instead I chose to be Miss Capable/Miss Independent who could do everything for herself and didn’t need a man in her life..but in truth desperately wanted one to come and rescue her from heavy life calamities.

Now I can use my softer vulnerable feminine strength to summon the male strength I need by letting down my defences and opening up and asking for help and letting the lovely men out there be just that…and take care of me.

I can’t wait to find out who is going to step up to the job and take care of me for a change while I relax into taking care of myself and the relationship…

thanks Bobbi

It’s taking time to let the vulnerable “little girl” inside me out..but she’s slowly emerging and taking over from “Miss Independent Calamity Jane”..

Love Suzi

love Suzi

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- bobbi August 26, 2013, 3:29 pm
  
  Hi Suzy! Thanks So much for sharing your story. Love the Calamity Jane reference!! Keep up the good work – it takes some time to change old habits. It’s SO fun and lovely when you allow yourself to be a girl. Enjoy!
  
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Trixie February 24, 2012, 3:50 am

I am learning so much about myself, dating and men, through Bobbi, Rose, and Rory that I’m finding myself growing more mature and knowledgeable every day in hopes of finally finding true love and happiness!!! I have been in my masculine for many years…and I’ve also been in too many hurtful relationships as well. I am so grateful to have happened upon these ladies and appreciate all they are teaching me 😉
Thank you Bobbi,
Trixie

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- bobbi February 24, 2012, 11:49 am
  
  Hi Trixie. I can’t tell you how wonderful it is to hear this from you. It’s really fun being a girl, isn’t it?? Rori and Rose are so special and I’m honored to be counted among them. Keep reading and keep learning. And make sure you give yourself a big atta-girl! You should be really proud of yourself.Keep in touch.
  
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Beth Luwandi February 18, 2012, 9:13 pm

I’d be honored, Bobbi, to have you quote me in your blog. I think this is such important work! While I had done tons of counseling over the years of a really difficult marriage, it wasn’t until I started engaging this kind of process that I truly had a break-through. I’ve never had a better life!

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Beth Luwandi February 17, 2012, 10:44 pm

I have to say, I have been learning about and exercising my feminine energy for more than a year and it has revolutionized my life and relationships. I was born very female and it is such a relief to walk in the strength and confidence of who I truly am. There’s nothing subservient about being true to myself and allowing the men around me to be masculine. Real men don’t hurt women and when I behave like a real woman, the real men separate themselves from the boys. In that way, it becomes easy to take care of myself… but not in a bitchy way that insults men and keeps them at arms length. Bobbi is right on.

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- bobbi February 18, 2012, 8:09 am
  
  Wow Beth! You said this so beautifully…I couldn’t (and didn’t) say it better myself. I’m so happy to hear you have been mastering this. It’s easy once you give into it, isn’t it? And SO delightful. Men are wonderful creatures if you let them be. If you don’t mind I would like to use your words in a future blog post. They are just perfect. So glad you stopped by and shared your feelings here.
  
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Innocent Bystander February 6, 2012, 8:30 pm

I like the idea of having a script for those hard/awkward conversations. I can see how this could apply to non-romantic relationships too.

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Suzanne December 3, 2011, 7:49 am

What about in the case where a woman makes a comment that shows her as pushy, and the guy stops communication with her? Should the woman apologize for her actions, or should she just give the guy some space?

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Drew February 10, 2011, 7:06 am

“You obviously believe in patriarchy, but the best relationships and marriages lean strongly towards the egalitarian.”

When the buzzword “patriarchy” is used, it’s a clear sign that the author leans towards misandry and a political ideology that has nothing to do with honest and intimate relationships.

Let’s keep the politics out of dating and the insults out of the dialog.

While the social expectation is one thing, our essential biological nature is revealed most clearly in the context of dating and relationships. Biology strips away all the nonsense of unrealistic social expectations and truly gets to the heart of the matter.

Kathleen has a political agenda and cares little for honest and the truly intimate relationship between a man and a woman. Ignore her.

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- Bobbi Palmer February 11, 2011, 2:50 pm
  
  Thanks Drew. Very insightful as always. I love the conversation!
  
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Bobbi Palmer February 1, 2011, 9:12 am

Good advice as usual Drew! I should have put that in my post: the one exception to telling him what you want is with relationship qualification. In that area you are always safest letting him take the lead. When he’s ready to tell you he wants to go to the next “official” step he will. Meantime, Drew’s list of signals are right on. Does he act like he wants to make you happy? Unless you are at a point where you are willing to leave the relationship if he doesn’t return your feelings, I’d stay quiet and enjoy it for now.

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Drew January 31, 2011, 6:09 pm

Warning, “relationship” talk usually causes a short circuit in a man’s brain.

Rather, what are his actions regarding your relationship? Men often speak through actions. Is he there for you? Does he show affection, respect, passion? Does he contact you for no reason except to see how you are doing? Does he compliment you and worry about your emotional state?

If you answer “yes” to these questions, you don’t need to ask him about the relationship. You have one and it’s strong. Enjoy it and don’t jeopardize it with a question that will short circuit his brain.

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Kathleen January 31, 2011, 11:23 am

“I’d like to go out. How about Sunday?” is not a pushy statement. If a man has a problem with that, he doesn’t have a right to date.

If a man has a problem with a woman saying, “I’m not ready,” he is not qualified to date.

You have a double standard of kindness for women and men.

Bobbie, you are a male chauvinist.

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Kathleen January 31, 2011, 11:19 am

It’s obvious that you think the man should dominate the woman. You’re setting women back a thousand years.

Your website is very demeaning because you blame all dating problems on the woman.

If your husband is such a great guy, he should educate other men on how to be equal dating partners to women.

You obviously believe in patriarchy, but the best relationships and marriages lean strongly towards the egalitarian.

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- Bobbi Palmer February 1, 2011, 9:39 am
  
  If you read ALL my articles you’ll see that:
  1) I ALWAYS tell women that if they aren’t being treated with kindness and respect from a man to run the other direction. In fact much of my coaching work involves teaching women how to flee from jerky guys and stop picking them.
  2) All my advice to women is predicated on the fact that you are trying to attract a “good guy.” If that’s the case, then kindness to him is certainly in order.
  3) My work — my passion — is helping women find love. This website is dedicated to that purpose. So when I focus on women and areas where they can shift their thinking and behavior..that certainly doesn’t mean I blame them for all the problems. It just means that I think they are here to learn about what THEY can do to find a fulfilling and loving relationship. They aren’t here to learn about what the guys are doing wrong.
  
  Oh and last thing: your comment about my husband is remarkably like a previous comment I received. That my husband makes his living doing something other than coaching men hardly warrants your snide comment. You may find this too girly for ya, but here goes: I support my husband in anything he does. I am his biggest fan. Knock off insulting him please.
  
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- jeanine February 17, 2012, 7:05 pm
  
  you don’t know what you are talking about. I’m a homicide prosecutor, not exactly the type of girl to take a back seat to any man out there, and Bobbi’s advice is spot-on. It is possible to be strong and still let a guy be a guy. I’m guessing you are of the “men are intimidated by me because they can’t handle a strong woman” school of thought. Let me translate that for you: men don’t like you because you are a pushy you-know-what.
  
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LJ Maggie January 28, 2011, 3:33 pm

This post is perfect for me right now. I am trying to figure out how to ask the guy I have been dating for four months, where this is going. Still not sure how to ask him.

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- John October 24, 2013, 7:09 pm
  
  (Bobbie, I don’t want to step on your toes here. Please delete this if you wish.) My advice: Don’t ask him where this is going. Stop making yourself TOO available. If you are right there with him, for him, in his life, ready to be whatever he wants you to be, then you are, frankly, being too easy. Why would he want to take this relationship anywhere else? He’s already getting everything HE wants out of it. Instead, fill your calendar with things that purposely EXCLUDE him, and get on with making a wonderful life for your SELF. When he sees you are not around as much, he’s gonna start looking for you. And that’s where YOU have the upper hand in the relationship. At that point, YOU get to decide if he is worthy enough for YOU. You have an unbelievable amount of power in the relationship. Don’t just hand it all over to him. He may not actually deserve it.
  
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