Why Am I Not Getting a Second Date? (3 Reasons from a Matchmaker)

Dating can be exhausting and emotionally draining, but it is a necessary step in finding long-lasting love. 

As a matchmaker and relationship expert, I’ve been helping singles navigate the dating scene for the past 26 years. I’ve seen people of all ages and backgrounds have trouble, and my job is sometimes to help them get out of their own way.

This gay man posted on Reddit that he is in his 40s and seeking a committed relationship, but he can’t get past the second or third date. 

There are a couple of scenarios going on here, so let’s break it down.

We have all heard that you must kiss a few frogs before you find your prince, and this is often true. Many people go on a ton of dates (even second or third dates) that don’t end up being right for them — and then they end up in a great relationship. 

Dating is like shopping. You need to try things out before deciding if you want to keep them or put them back.

After a couple of dates, the other person has decided that he is not the right fit. That’s OK. He needs to continue meeting people and exploring if they are right for each other. Ultimately, this will bring him closer to finding his person.

If this guy finds himself falling for people after a couple of dates and then ends up disappointed when the other person doesn’t feel the same, he may have to look at his standards and expectations for a potential partner. 

He may be setting the bar too low and considering people who don’t align with his values as potential partners.

He may be having long conversations but failing to address relationship goals and expectations. This could be a case of not asking the right questions to vet potential matches. Questions like:

• What are you looking for?
• Do you see yourself married or single 10 years from now?
• Have you been in a committed relationship before?
• What qualities are you looking for in a partner?

Maybe if he asked these dates what type of relationship they were seeking, they might have replied that they were simply looking for a hookup or friends with benefits.

Being a great dater is about learning to ask great questions, and my bet is that he has failed to ask the right questions to properly screen his dates.

We’ve all had friends who see the good in everyone. They don’t recognize the red flags that we can see from a mile away. If his friends can easily tell him how they recognized his bad choices from the start, it may be time for him to let them select potential partners for him rather than choosing himself. 

There are professionals that offer “online takeover” services to manage dating apps for their clients. Sophy Love offers a dating concierge service that helps clients revamp their dating profiles and what they are looking for in a match.

Instead of asking Reddit for help, this gentleman might want to consider outsourcing his swiping to the professionals to get in front of better quality matches.

He may be experiencing dating fatigue and frustration to the point where it’s time to take a break from dating and then start again in a few months with a fresh perspective. Dating from a place of power, with confidence and optimism, will guarantee he is putting out good energy to attract the right partner!