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How to Talk to Older Women


Taken from Patsy Mennuti's / Hella Cougar's manual How to Meet & Date Older Women


You've made an approach IRL or you've slid in, and you've got an older woman's interest. Before you ask her something dumb like, "Do you like raccoons?", read the following. This will also help you move beyond, "Hey, WYD?" and "How was your day?"


One of the things you need to know about older women is that many, if not most, will want some basic level of conversation. We really are interested in you and your life! And while many older women will be able to carry the conversation, it's really helpful when a young man can also pull his weight.


So here are the elements of adult conversation:


You are actually curious about the other person and who they are. Your questions / exchange reflect this.

Your questions are framed to elicit more than a yes/no response. They invite the other person to elaborate on a topic.

Your questions aren’t formulaic. They flow into other questions. It’s kind of like getting lost on an adventure.

Your listening is your guide along the path. Good conversations are equal parts listening and talking. Staying in your head about the next question you will ask won’t allow a flow.

Your answers to questions aren’t basic and short. You can actually articulate thoughts and experiences.

You don’t monopolize the conversation.

Your questions and conversation will establish connection and commonality. Like igniting sparks of interest or at least new avenues to continue down with your relating.

You bring fun, humor and interest. You are engaging and dynamic in your unique way.

You maintain eye contact to stay focused and engaged (and it helps with active listening).

Silence or breaks in the convo is acceptable, too!


A note of caution: Don’t be annoying or intrusive with your practice of adult conversations.


Here are some light conversation topics:

Travel (What’s on your bucket list? Where have you traveled? Favorite places?)

Hobbies & Interests (What do you like to do in your spare time? If money was no object, how would you spend your time? Favorite places to go out / eat?)

Advice (What kind of sheets? Comforter? Soy creamer? Chicken? How do I …? Where do I find …? Knowing what you know, what would you do?)

Geographical (Where are you from? Where have you lived?)

Biographical (Where did you go to school? What did you study? How have you spent your life?)

Career (What kind of work do you do? Do you like it? What is your dream job? What was your path?)


If this is going well, you can navigate further in a RESPECTFUL way. She may or may not want to go there. I wouldn’t do these in a casual approach in the grocery store. Only over drinks, dinner, etc. Respect privacy and confidentiality. I am usually the one asking these. I am a very curious cougar.


Heritage (Italian, Mexican, Jewish, Haitian, South African, etc. Be careful how you ask this.)

Relationship history (Partners, husbands, boyfriends)

Struggles / adversity / navigating tough times

Kids (How many? Challenges / joys in raising kids)

Drug / alcohol use (Experiences, preferences, experimentation)

Politics (This can be a hot potato and can totally wreck a vibe in my experience. However, some women may want to know how you are aligned before they go any further.)

Faith (I love to talk to guys about faith – if they grew up with a particular faith, is it still strong, what their beliefs about something greater are, what happens after we die.)

Sex (I also love to quiz guys on their sexual history. What they like, don’t like, their experiences, attitudes about sex, what we can explore. I would tend to err on the side of letting her bring this up. Otherwise you come off as a bit piggy. Def don’t tackle this too early in messaging. It’s a HUGE turnoff. I usually only launch into this if we’ve explored other topics, and I’m interested in them.) Don’t EVER ask body counts as discussed previously.


By the way, practicing adult conversations with men (or friends) can help with being a good conversationalist with women. Here are some practice ideas in general:


Get a job or mentor where you are interacting with adults (golf pro shop, country club, restaurant, tennis center, hotels, really anywhere adults are working and you can interact with them primarily instead of young adults).

Just practice light conversation with adults at the store with the cashier, in line, in the aisle, at the gas station, at the gym, your parents’ friends, etc. Even if it’s just a simple exchange.

Start to notice when adults are around and just freakin’ talk to them.

Run an errand for your parents. It will give you the perfect opportunity to practice asking for advice.


By Patsy Mennuti, Hella Cougar | Taken from How to Meet & Date Older Women: The Manual

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