How to Start a Conversation with an Older Woman

Online dating is stressful, no doubt about it. You may have the looks to attract a woman to your profile, but good conversational skills are required if you want to keep her interested.

You want to create a natural back-and-forth dialogue between you and your prospective lady. It shouldn’t feel forced, and you shouldn’t feel like you’re trying to come up with the next line to type.

You might be a wordsmith, but if you’ve met someone who isn’t, at least not online, this can  be challenging. Here are tips to get things started and to keep things flowing:

Ask about her passions. You’ve read about them in her profile, so now you can ask specific questions that she’ll love to expand on. If there’s one that you have in common, even better. This shared interest could be an idea for your first date.

Show an interest in her work. Likely, this will be a large part of how she spends her time, and she’ll have plenty to say that will keep the conversation flowing.

Express an attention to detail. Find something in her photos to comment on. For example, you see a place in the background you recognize (that you’ve been to), or she’s wearing a band/sports shirt you have an opinion on. Women love a man who notices the little things.

Talk about her kids. A lot of older women have children. Don’t think because you’ve just met (and not in person) that’s it’s too early to bring them up. She’ll love you asking about their ages, interests, and her mom challenges.

Mention your family. Women are attracted to men who are close to their family. It’s also nice to share familiar struggles with someone who hasn’t heard the same story a million times.

Now that you have a few pointers, go for it! Be real, be honest, and focus on her. Listen to her words and refer back to them in the ongoing conversations (emails, texts, IMs)

Guys: How do you start a conversation, and how do you keep it going?

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