Guest Post – 8 Online Dating Message Tips to Get You a Date with an Older Woman

by Monica David

If you’ve started your quest for older women online with the but haven’t gotten anywhere, don’t be discouraged. Dead-end chatting or an absence of responses may make it tempting to give up online dating. But for those who are willing to put in the effort, the results can be well worth it.

A May 2017 study showed that 20 percent of current relationships began online, so it’s definitely a vehicle worth testing out. However, it’s challenging enough to figure out how to get the ball rolling with women your own age. If you’re interested in connecting with older women online, what can you do to increase your chances of getting actual dates with them?

8 Online Dating Message Tips to Intrigue Older Women

To help you find success getting dates with older women, we’ve compiled a list of online dating message tips that can take you from staring at a computer screen to looking into the eyes of a beautiful older woman. Check out these dating sites for help to meet your own cougar if you are not sure where to start.

Build a rapport but don’t take too long

Younger guys see attractive photos and immediately want to get physical. It’s wise to take a pause, though. Patience is an important part of securing a date with an older woman.

Younger women may be used to the instantaneous dating culture but older women need to feel comfortable with you online before agreeing to spend time with you in person. Your first message to an older woman should not include a date (or hookup) invitation.

This doesn’t mean that weeks of chatting are required. In fact, dragging out the online messaging process can actually have a negative effect on your ability to score a date.

With cautionary tales of fake dating profiles swirling around, it’s important that a woman knows that you are who your profile says you are by creating an engaging online dating profile. If she’s been getting messages from you for weeks without any mention of actually meeting, the red flags will probably go up and she’ll stop responding.

She’ll also want to see if there’s chemistry in person before getting too wrapped up with you online. You need to tactfully get to the first date in an efficient manner without rushing past the stage needed to establish a rapport.

After you’ve received her response to your initial message, you’ll only need a few more exchanges before getting to the date part. Try and keep the back-and-forth limited to 3 to 4 times. If she’s responded to you a few times, she’s obviously at least a little bit interested, so you have the encouragement you need.

However, if her responses are short and icy, you’ll get a chance to decide whether this is someone you feel comfortable asking out anyway. The rapport-building stage gives you both an opportunity to decide whether or not you really want to meet each other.

Use your messages to show you will be good company

If an older woman is going to spend her valuable time with you, she needs to have a reason to believe it will be worth her while.

If your messages are monosyllabic and expressionless, she probably isn’t going to assume you’re a great conversationalist in person. Therefore, one of the key online dating message tips is to give an older woman the impression that you’ll be a good date.

An older woman will appreciate getting a feel for your personality when you write to her. Whether through witty banter or empathetic remarks, you can show a bit of who you are in a message. If she enjoys what she’s getting so far, she’ll want more of it in person.

Be careful to not seem too self-obsessed when presenting yourself to an older woman. Ask questions about her and respond with genuine interest.

If your online messages seem completely centered on you, an older woman most likely won’t want to sign up for an in-person extension of that. If she sees that you care about getting to know her, she’ll be more willing to give you a chance to do so.

Gradually increase her excitement for you

Figuring out how to get a woman interested in you can be tricky. One of the most nuanced online dating message tips is to subtly and gradually increase the anticipatory energy between you and an older woman. This isn’t as complicated as it sounds.

The idea is to tease just enough excitement out of her that she truly can’t wait to meet you. This involves the subtle art of sprinkling intrigue into your messages.

You might mention some interesting aspect of your life, but brush over it quickly.

Or you could respond to something she says with “I definitely relate to that” and make her wonder how.

Gentle compliments with just a touch of flirtation can be tucked into messages as well. She may melt a little or perhaps feel a rush of excitement.

She should be feeling more and more interested in meeting you with each message you send, so when the one asking her for a date arrives, she won’t have to think twice about her response.

Ask her out in a mature and gentlemanly way

Sometimes younger guys try to shield themselves from the risk of rejection by masking a date invitation with some half-assed statement like “let me know if you get bored this week.” Um, no. That’s not the way to let an older woman know you’re interested or to make her feel excited about you.

One of the most obvious – yet somehow commonly underutilized – online dating message tips for pursuing an older woman is to make it clear that you’d like to go out with her.

Bite the bullet and ask if she’d like to do something with you, and phrase it in a mature way. Please don’t ask her if she’d be down for chilling. It highlights the age difference when you choose slang over traditional word usage.

Ask her if she’d like to have coffee sometime this week or say you’d love to meet her in person and ask what her schedule is like. You need to be willing to risk rejection if you want to increase your odds of acceptance.

Don’t be overtly sexual

The next of the online dating message tips is a natural complement to the previous one. When asking an older woman for a date, make sure it doesn’t sound like a sexual proposition.

She hasn’t met you yet. She doesn’t know if she’ll want to have sex with you soon after meeting or many dates later or absolutely never.

Leading with sexual statements shows that’s primarily what you’re looking for and puts the expectation out there that it’s going to happen. An older woman does not like to feel pressured into anything. So, if she senses that you’re looking for a sure thing, it’s likely to make her feel very uncomfortable. Listen, she may want to get sexual with you, but leading with it smacks of immaturity and desperation.

She wants to know she can have a nice time with you, whether or not there ends up being any sexual chemistry. She also doesn’t want to feel like a piece of meat. So keep sex out of the initial date suggestions.

Don’t frighten her off with too many plans at once

Sometimes men get over-eager when they see an online profile that draws their attention, and even more so when they get a response. They then occasionally get a little carried away with the date ideas.

One of the online dating message tips that should be given special attention is to keep the date suggestions simple and brief. It’s likely to scare an older woman away if you lay on too much at once.

For instance, telling a woman you haven’t met yet that you’d like to go rollerblading with her, and then out to dinner and a movie, followed by going back to your place for wine and cuddling is pretty much guaranteed to scare her away.

A first date should be very simple and relatively brief. This is why coffee or cocktails are so popular for the occasion. The time commitment is low and it really should be when you have no idea how you will feel in this person’s presence.

You also don’t want to talk about a succession of dates before you’ve even had one. You may think you’ll love being with this older woman and vice versa, but you really don’t know until you’ve met her. So don’t start planning the second and third dates before you have the first.

Not only would that approach likely overwhelm the woman with undue pressure, it also could create an uncomfortable situation later on. If one or both of you end up not feeling the other, it’s very awkward to already have tickets to go to an event together the following week.

Definitely take it one step at a time.

Suggest meeting at a place that would be convenient for her
If your date suggestion sounds safe, comfortable and convenient, it’s more likely that you’ll get a “yes” from an older woman.

Don’t offer to pick her up. You may think you’re being gentlemanly, but remember, at this point you’re a total stranger. She doesn’t know if she’s safe getting into your car and she certainly doesn’t want a stranger knowing where she lives or works.

Of course, she can just tell you she’d prefer meeting somewhere public, but why put her in a position to have to say that?

She might even be concerned about the fact that you wanted to pick her up. That alone might turn her off of a date with you. It may sound paranoid, but an older woman has seen, heard and been through enough to not immediately trust random strangers from the internet.

When deciding on a location, suggest places near her part of town or ask where she’d like to meet. She’ll feel more comfortable if she knows the place or at least the neighborhood. If she can get there and back home quickly, it’ll be a lot easier for her to say “yes.” It will also show consideration on your part. The willingness to go out of your way to see her will be noted.

Start a conversation that can be finished in person

The last of the online dating message tips that will lean the odds in your favor is to begin a conversation online that you can finish offline.

While you’re building a rapport with an older woman, there are probably topics you can expand upon. Don’t do it in writing. You’ll miss a huge opportunity to lead the conversation directly to a date.

For example, let’s say you have commented on a woman’s photograph with monkeys in Bali. You might say that reminded you of something funny that happened during your trip to Thailand. She could reply that she’d like to hear it. You then may say that you’d love to tell her about it and ask if she’s free for coffee that week.

Also, any question she asks that you have a long or even longish answer to can be an easy opportunity to respond, “It’s a lot to type. I’ll have to tell you in person.”

You can easily segue into asking for a date at this point and you’ve taken the edge off of first-date anxiety that often arises over not knowing what to talk about. You’ve set the stage for an interesting conversation before you even show up for the date.

These online dating message tips should get you off to a good start. Happy messaging and happier dating!

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