An older woman likely knows what she wants and doesn’t want. Be patient and allow things to develop naturally before you ask her out. If you’ve already been friends with her for a while, then you know that you both have chemistry and a connection, which is a really great thing. If you end up chatting over text, don’t tell her your exact age—instead, give a vague answer, like “not old enough to be an awesome person. " This creates a sense of mystery and forces her to get to know you for who you are.
A nice pair of jeans or slacks and a clean button-down shirt are always a safe bet. Complement your look with some brown or black dress shoes rather than sneakers to take your look to the next level.
For example, if she’s a big John Mayer or Michael Bublé fan, you can try to get tickets to a concert if they’re coming to your area. Don’t stress about it too much. Sometimes simplicity is best. For instance, if she loves Mediterranean food or poetry, you can make a reservation at a restaurant or look for poetry readings you can take her to.
Put your phone on silent, too!
Start with a simple request to talk to her like, “Hey, do you have a quick second to talk?”
For instance, you would approach her and say something like, “Hey, how are you?” After she responds you could try a compliment like, “You look really good,” or something more specific like, “I love the way you style your hair. ”
For example, you could say, “I’ve got 2 tickets to the concert on Friday, do you want to join me?” or “I’ve been hearing great things about that new Italian restaurant, let me take you out Friday night and we can see if it’s any good. ”
For instance, if she asks something like, “Oh, will it just be me and you at dinner?” You can say something calm and confident like, “Yes, I’d like to spend some time with just the two of us. ”
If she says something like, “I’m not sure. I don’t know if I’m interested in dating right now. ” You can say something like, “There’s no pressure. It’s just a fun night out. It’ll be a good time, I promise. ” If she’s worried about other people, you can say something like, “Who cares? It doesn’t bother me. We’re just having a good time. ”
If she tells you that she isn’t interested at all, then don’t try to push the issue or you could come off as overly aggressive or like you’re harassing her. Keep it simple and say something like, “No problem at all. I completely understand. ”
