Online Dating Dilemmas

As matchmakers we encourage our clients to maintain dating momentum by staying socially active and experimenting with online dating. Lately, we’ve heard a string of stories from women about uncomfortable interactions they’ve experienced online dating. Though their experiences were different, each explanation ended with the same request.

Women want to know how best to respond to premature sexual conversation, advances, and explicit pictures they receive from random online dating experiences. And, even more – is there a way to improve their overall digital dating experience?

The Set Up

An online dating connection sometimes evolves into a string of witty banter and general get-to-know-you messages inside the digital dating app. If all is going well, the pair feel ready to move communication offline and make arrangements for an in-person meet-up. This is where things can get a little dicey.

Sometimes both parties act mature, respectful, plans are made, and standard first dates happen. Other times insinuations are made about the type of playful get-together you’ll have. Or sexually explicit language is used to pay you a compliment. One woman told us, “I exchanged numbers with a 41-year-old man and was shocked to receive a photo from him less than three hours later. He was only wearing his underwear, and the message offered me ‘something to think about’ while I finished my work day.”

If you’re solely into the hook-up culture, then that’s probably not disheartening to hear. However, if you’re a busy professional genuinely using dating apps to find a real connection you understand the frustration. What’s even more alarming is the consistency with which such disrespectful dating actions occur.

The same woman quoted above received a boldly presumptuous text the very same day from another guy with which she was planning a second date.

So, how do you best handle it?

As a woman – or man – who receives explicit images or inappropriate messages during the very early stages of dating it’s easy just to block the person’s number and move on. Unfortunately not addressing these sorts of behaviors only perpetuates the problem.

It’s important to respond to such messages for a few reasons.

  1. You are not a victim. Don’t allow someone to speak to you in a way that makes you feel less than.
  2. If he/she is sending these messages to you, then they’re most certainly sending them to others.
  3. If we don’t accept responsibility for creating the dating culture we want to participate in, then it’s not going to change for the better.

Now that you know why to respond, it’s important to understand how best to get your message across.

Shaming and name-calling are not the answer, but communicating what you’re looking for in a date is. Lead by example and remind this person the attractive qualities that will get them somewhere with you.

Here’s a script to get you started.

Think about what’s important to you and tweak the message to make it your own. The key is to show respect while articulating how you expect to be treated.

Uh oh! It looks/sounds like we’re not on the same page. My intention for using dating apps is to meet mature men who show up, respect me, and engage in an experience where we have a good time exploring a connection and potential chemistry. Sex is not part of the equation until all of those boxes are checked. If that’s not your thing, then we’re not a fit. No hard feelings either way.

Once you text or vocalize your intentions, the ball is in their court.

Don’t text again. Don’t keep talking. You’ll find out who this person is by how they respond to you.

Unfortunately, men and women are equally cynical about online dating. As a result, many tend to fall into a negative pattern of dating behavior. Upon receiving your thoughtful response, they might feel embarrassed for having sent the inappropriate photo or message in the first place.

Often times they’ll offer an apology and then ghost you. And that’s okay! Be grateful you spoke up and didn’t waste your precious time. We promise your empowered action made a positive impact on the greater dating culture.

On occasion, you’ll receive both an apology and a request for a date. In that instance, a friendly phone chat is essential to feel out the connection and potentially make a plan to meet. Your gut will tell you whether or not you want to go on a date with the person after that.

Whatever you do, don’t get discouraged!

We asked Kelleher’s Director of Matchmaking Kimberly Colgate to share some tips for increasing your chances of having a positive experience online dating.

I advise clients and friends who try dating apps to have fun and don’t take it so seriously. It can be a great way to discover what traits you are looking for in a mate and to whom you are naturally attracted. Online dating can be a cheap and easy way to get connected with a high volume of potential suitors. With that said, just because the medium is cheap and easy doesn’t mean you have to be. As you swipe left and right know that it takes time and effort to filter out who is on the same page as you.


When you do find someone that you think has potential reach out with the goal of actually connecting in-person. If you want a live, romantic relationship, then your actions should be in sync with that. Texting or sending messages back and forth for an extended period won’t achieve the results you desire.

Kimberly’s suggestions for improving your overall online dating experience:

  1. Know what you want going in. Remain open-minded and light-hearted.
  2. Don’t engage in text conversations for an extended period. Just meet.
  3. Keep the first date casual and flirty. Know your worth and act accordingly.
  4. If at any time you feel uncomfortable or something feels off, likely they are not your person.

Digital dating isn’t easy and requires an extra level of awareness and a few extra hoops to jump through to make sure you’re meeting quality people looking for a real relationship and connection. Kimberly adds, “Just because someone is not in the same place as you are is not an attack on you or them, so it’s best to move on quickly. There’s a lid for every pot and yours is out there looking for you.”

If you’re disgruntled with dating apps, we encourage you to learn more about modern matchmaking. Kelleher International performs in-person interviews and conducts background checks on every member of our elite network of singles. We also ensure you’re going on dates with matches who are looking for long-term partners just like you. Call or message us to learn more.