Establish a connection with her.
Find out if there’s chemistry between you before you ask her. Don’t simply approach an older woman that you’re attracted to and ask her out without ever having spoken to her. Take some time to have a conversation to see if there’s a spark or a connection. If you ask her out too soon, you could blow your chance! 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.
Dress well when you plan to ask her.
Show her you care about your appearance. You don’t have to put on a 3-piece suit, but you also shouldn’t be wearing sweatpants or dirty clothes. Put on a nice, clean outfit, wear some good-looking shoes, and fix your hair. Take some extra time to fix yourself up so you’re looking your best when you ask her out. 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.
Imagine what it will be like when she says yes.
Envision success to help boost your confidence. Picture in your head that she’s going to say yes whenever you ask her. Imagine how good it will feel and how happy you’ll be. Keep that image in your head as you prepare to ask her so you seem self-assured. Avoid the temptation to think about worst-case scenarios or mistakes you could potentially make. Envision success and make it a reality!
Plan out a date based on her interests.
Take her somewhere you know she’ll love. Get to know more about her and what she’s passionate about and interested in. Tailor your date night to her interests so she’ll have fun and she’ll be more likely to say yes when you ask her. It can be fun and silly or it could be fancy and formal—it all depends on what she likes. 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 away.
Give her your full and undivided attention. Even though it may be commonplace for people nowadays to be on their phones pretty much all of the time, an older woman may see it as immature. Plus, if you want to show her that you’re serious, give her your full attention and keep your phone in your pocket. Put your phone on silent, too!
Be confident when you ask her.
Even if you don’t feel it, try your best to fake it. It’s totally normal to feel nervous, but confidence is key. You also don’t want to come off as arrogant or cocky, so try to find a balance. Try to be as calm and polite as you can be, and if it helps, just pretend that you’re super relaxed and confident. Start with a simple request to talk to her like, “Hey, do you have a quick second to talk?”
Compliment her appearance.
Tell her how good she looks so she knows you’re interested. You don’t want to just approach her out of the blue and ask her out. Take some time to talk to her and say hello. Give her a nice compliment about the way she looks to start hinting that you’re attracted to her. That way when you ask it’ll seem like a natural progression. 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.”
Tell her you want to take her out.
You don’t have to call it a date. You also don’t have to beat around the bush, either. Be direct and tell her about an event or a restaurant you’re going to. Then, ask if she’d like to come with you. But make it clear that your interest is romantic. 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.”
Listen to her when she responds.
Let her know that you care about what she thinks. She may be hesitant or she may ask you questions about your intentions. Don’t brush her off or get impatient. Pay attention to what she says or asks you and respond appropriately. 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.”
Reassure her if she has reservations.
Tell her that you don’t care about the age difference if she’s concerned. Because you’re younger than her, she may not be sure how she feels about going out with you at first. She might be worried about your intentions or about what other people may think. If that’s the case, tell her that you’re attracted to her and that you just want to spend some time with her. Show her that you’re genuine by being honest and taking the time to reassure her. 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.”
Don’t take it personally if she says no.
Respect her wishes and don’t dwell on it. It may not feel good to get rejected, but you shouldn’t react angrily or get upset. Besides, it could just be the timing. She may not be interested now, but if you respect her wishes, things may change in the future, whereas if you storm off, it could ruin your chances forever. 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.”
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