date with MILF

Dating an older woman can be tough. She’s got baggage and she might not be as hip to the new dating trends as you are, but that doesn’t mean her heart is any less open than a younger girl’s. So if you’re looking for tips on how to date an older woman, we’ve got just the thing for you: here are some of our top tips on what to do and what not to do when dining with your potential sweetheart.


-Pay the bill. Period. She may offer to split it or pay for her own meal but you must insist on paying and do so without question and without any discussion about who pays. Don’t hesitate to spend some money on her. She might giggle and tell you not to worry about it, but insist strongly that this is your treat!

-Use your early dates to really get to know each other. So that means small talk is fine, but make sure you also ask her deeper questions about herself and her life. We asked some of the members of the dating site MILFMaps for this advice, and nearly all of the ladies here prefer deeper questions to get to know their date.

-Introduce her to new things in your life and let her share hers with you in return. You don’t have to like each other’s hobbies but the important thing is that you’re willing to try them at least once and give them a shot.

-Do listen carefully when she answers any questions you ask! This is where all those deep conversation about herself will come in handy. Make sure you’re listening closely so that you know exactly what she likes and doesn’t like and why. That way you’ll be able to give her the best experience possible.

-Don’t let the conversation lag. If you’re having a hard time finding things to talk about, try asking her open-ended questions about any new experiences she’s had that made an impression on her. Even if it might seem like there is nothing that interesting or new going on in her life, don’t underestimate the power of good conversation.

-Don’t forget your manners! She may not want to go out for a formal dinner, and that’s perfectly fine, but manners are always important in any situation. Don’t curse or talk down about others and show her how respectful and kind you can be at all times.

-Do compliment her on both the food she orders and on herself if you think it’s necessary. Make sure your compliments are sincere but don’t make them too personal or too suggestive because this could make her feel uncomfortable.

-Do try going to a nice lounge or bar instead of a fancy restaurant. That way, nobody will feel out of place and yet there will still be good food and drinks available! Sometimes all one needs is a change in scenery from time to time so make sure you help her remember this date for all the right reasons.

-Do show her that you can also be a gentleman too! There’s nothing wrong about opening doors for an older woman and treating her like the lady she is, especially if she deserves it after all those years of hard work. It’s a way of showing that you respect women and their choices in our modern world.


-If she says “no” to something you want, don’t push any harder! For example, if she says no to another drink and you decide to order it for her (despite her protests), that can be a big mistake. It’s either she wants the additional drink or she doesn’t: forcing her into it will only make her feel like you’re trying to tell her what to do and how to behave.

-Don’t let yourself be intimidated by an older woman! Sure, they’ve got more experience than younger girls but that’s not always such a scary thing as everyone seems to think. What matters is how mature someone is and people of all ages can have the same level of so don’t be fooled by the age on someone’s ID!

-Don’t hog the conversation all night. You’re a great conversationalist but that doesn’t mean you need to talk for 90% of the time and let her interject a few words here and there, if at all! She might not be as experienced in dating as you are, but she deserves a chance to prove herself too!

-Don’t take her back home already after your first or second date. Try taking things slow and let your relationship develop more naturally. If you’re on the same page romantically, then there’s really no reason to rush things. Besides, maybe she’ll invite you home with her!

-Don’t be afraid to take control of the situation! You don’t want to come off as too pushy or imposing but sometimes little gestures like opening doors and such can go a long way into making her feel cared for and respected—and that can lead to great things!

-Don’t make her feel like she’s being interviewed! This is a date, not an interview, so let the conversation flow naturally. No need to ask all these questions you would normally never think of asking in real life, unless you want to come off as nosy or too serious with your approach.

-Don’t forget that women are people too! You don’t have to treat her like royalty or anything but it certainly wouldn’t hurt if you made the effort to respect the older woman you’re out on a date with. Try asking her what she likes instead of assuming things about her tastes and interests.


Remember that women, no matter how old they are, want to be treated like human beings. They’re not here for you to impress and/or pamper them but just because they’ve reached a certain age it doesn’t make them any less deserving of respect or affection than younger girls. Sometimes all an older woman needs in her life is a man who can see past what society labels as “old” and instead appreciate what’s on the inside: their personality and character.

So there you have it! Everything you need to know about dining out with an older lady in one article! Remember not to overdo things and keep the mood light (and non-sexual) when possible; this isn’t about winning her heart through means of a lovesick puppy, but about providing her with a great night out that she’ll remember fondly.

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