Dating conversation starters: what to say to an older woman


March 26, 2008 – 4:02 pm

Often when you date anyone you have met online, it can be difficult to come up with things to say. This is especially true when you’re trying to date an older woman.

The only way that you have to show what type of person you are and to prove your worth is through your conversation skills.

If you are lacking in this department, you might find the world online to be lonely. If you excel, on the other hand, your inbox could be full 24/7.

When it comes to talking about themselves, many people do quite well. They can ramble on for hours if you let them, but it doesn’t make them likeable.

The same is true when it comes to online dating. You can talk about yourself until you’re blue in the face but it’s not going to get you a date. In order to win over a lady online, you need to be able to hold a two-sided conversation. The following conversation starters will help you out:

Ask About/Show Interest in Her Work – A career woman spends approximately 1/3 of her time at work. This is a big chunk of her life that you’re missing out on if you are not asking questions. When you first meet a woman, you should ask her what she does for a living. Have her explain it to you and try your best to get interested in it. If you pay attention, you will be able to ask her about specific projects and developments later on instead of using the generic “how was your day” routine.

Ask About Interests – You are likely already familiar with some of the interests included in her profile, why not use these to start up a conversation. For example: If one of her interests is hiking, you could ask her where she went hiking the last time. If you are not familiar with an interest, ask her to explain it to you.

If She Has Kids – Talk about her kids. Women love to share stories about their children. You can ask her about their first words, their grades in school, their funny stories…anything.

Family – When you’re trying to get to know someone, it’s always a good idea to share stories about your families. Ask how large her family is, if she has any siblings and how often they get to see each other. Don’t be afraid to talk about your own family. You can learn a lot about who a person is by learning about their family.

Younger men often try to woo older women with outlandish stories, but it rarely ever works. You can often get further with a few humble, honest words than you can with a whole list of accomplishments. Just be who you are. Show an interest in her and in everything that interests her. Stop and listen. Remember the things that she tells you and you will do quite well.