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First Date Ideas - Where To Take An Older Woman


When you are first meeting an older woman it is important to have a few solid first date ideas ready. As we discussed in our previous article on how to go from a phone call to a first date my favorite and most successful first date is a short drinks or coffee date. Drinks or coffee is the perfect first in-person date for a number of reasons:

Why do drinks or coffee on the first date:

  • It's simple
  • It's hard to say "no" to
  • It's cheap
  • If things are going well you can move to another spot easily
  • If things are going poorly you can end it and move on easily

Basically, drinks or coffee dates offer a lot of flexibility without much commitment on your part. You are not committing to spending several hours with someone you barely know, but are still getting to know them more. This is also a great opportunity to put yourself in the position of the one making sure she is good enough for you and not the other way around.

If you are still in the process of looking for someone great don't forget to check out both our favorite places to meet single older women as well as the best sites and apps to meet older women.

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Best For Relationships
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Best For Casual Fun
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Great If You're Handsome
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Tinder Highlights
  • Great if you're pretty good looking
  • Very popular, especially if you're 18-22
  • Really focused on photos
  • Becoming more of a dating than hookup app
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Below is a solid guide for generating first date ideas as well as planning and executing a great first coffee or drinks date:

First Date Ideas - Coffee or Drinks Date

First date ideas #1Pick the right location

When brainstorming first date ideas you want to find a place that has the right atmosphere and energy for an enjoyable conversation. For drinks, a lounge with comfortable seating and a quite enough atmosphere to hear each other well is perfect. Bars typically don't have a great atmosphere for a more intimate conversation and can be very noisy.

For coffee, an independently owned coffee shop with comfortable chairs is ideal. Chain coffee shops like Starbucks tend to be much brighter and less intimate a setting.

You also want to pick a place that has a lot of other fun or interesting things to explore near by. If the conversation is going well you want to have the option to immediately extend the coffee date into a longer encounter. Planning ahead this way can allow you to be "spontaneous" and transition to another fun place with ease.

First date ideas #2

Don't pick an expensive place

Most older women dating younger men are not expecting to be spoiled by them. If they wanted to have loads of money spent on them they would date older men with money to burn. You likely will be unable to keep up with that level of spending and you don't need to. Younger men dating older women have plenty of non-financial advantages already.

Aim for a place that has a little class, character, and intimacy over an expensive place. Especially on a first date you don't really know what you are getting yourself in to. You don't want to spend a lot of money on an older women if you don't even know she is worth it yet. As long as you don't go too cheap on your first date ideas (a cup of coffee at Dunkin' Donuts) you will be fine.

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First date ideas #3Ask her where she will be coming from

The older woman you are dating will be much more willing to commit to a first date and actually show up if you choose a location that is fun and CONVENIENT for her. You don't want to come out and directly say "what is your address?" but you want to at least know what part of the city or region she will be coming form.

When thinking of first date ideas you want to choose a location that is convenient for both of your will allow you the flexibility to either meet her at the location, pick her up, or even have her meet at your place first and then head out. All three of those options have their benefits and will depend on what your goals and strategies for the date will be.

First date ideas #4Pick a place where you will be comfortable

Coming up with a list of first date ideas for places you have never been to or would feel out of place in is a waste of time. You are most likely to attract a cougar if you are relaxed and having fun. That is most likely to happen if you are in a location where you are comfortable and at ease. That way, you can have a great first date conversation.

The whole goal of a first date is to find out if you are attracted to the older woman you are with and generate attraction. Your conversation is guaranteed to be better and your confidence higher if you are in a place where you feel at home. That is as long as you can avoid the topics you shouldn't talk about on a date with an older woman.

Single woman

First date ideas #5Have a backup plan

Before you ask out the cougar you are interested in make sure you have a few different options ready to go. Who knows what you can expect on a first date with an older woman. This is why having several first date ideas is so important. You want to be able to offer alternate ideas if your initial plan isn't going to work out. Maybe she doesn't drink, maybe she is allergic to coffee,  maybe her ex-boyfriend is a bartender at your initial choice. Doing a little extra planning at the beginning can pay off big later on.

The worst case scenario is that you have first dates planned for other women you will be meeting in the future.

A man with a plan who can also be spontaneous and fun is exactly the type of guy you want to come off as. Having several first date ideas will help a lot in this regard.

These five guidelines for brainstorming first date ideas should put you in a great spot when selecting a first date location! It might even make your date amenable to going on a second date.

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If you are still searching for older women to date check out our Best Online Cougar Dating Sites Review to find the best places to do so. There are a lot of scam sites out there that you want to avoid that can be hard to spot. You will also find Cougar Life reviews,Match.com reviews, and eHarmony reviews for those most interested in dating older women.


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