Portland Singles | Top 5 Date Ideas to Get to Know Him Better

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If you’re like many Portland singles, you’re probably feeling stuck in the same old dating routines – you know, the ones that leave you feeling bored and like you’re getting nowhere fast. You might be wondering how you can make a deeper connection and get to know your dates better from the start. Sound familiar?

Business people talking in office

Coffee and movie dates are good and all – okay, more like mediocre. But regardless how simple, casual, and low-pressure coffee dates can be, you need something better if you want to get to know him on a deeper level. If you want to reveal his true colors sooner than later, you’re going to have to put him to the test.

Today, our professional matchmakers here at Portland Singles Dating Service will reveal the top date ideas to get to know him better.

1. Somewhere you know he has to wait in line.

If you’re looking for someone with potential to last in a relationship and eventually get married to, you’ll eventually run into that “in sickness” line of the marriage vows. You don’t want to find out the hard way that who you thought was a gentleman is really an immature guy. Real life isn’t always fun and games. You want to ensure your guy is willing and capable of handling real life situations – and by that we mean annoying and stressful times.

How can you do this? You need to sell him on going to a theme park and see how he reacts to waiting in lines. Seriously, think about it. How annoying is it standing in the baking hot sun while inching along in the dreadful lines?

2. Somewhere he doesn’t go often.

Unexpected guests always seem to drop by at the worst times of the day, especially your favorite relatives, like nosy Aunt Martha. If he can stand in a line outside waiting for his favorite movie to come out, then he should be able to make a quick daytime run to the local pharmacy with you, right? Why not try a date at a local painting studio and see how he reacts? Or perhaps you can do something else along the same lines, such as dance lessons or cooking classes.

3. A restaurant…

Wait, what? What happened to the non-traditional date ideas? Stay with us here. A restaurant may seem like the typical date idea, but you can tell a lot about your guy from this date. Pay attention to how he talks to everyone in the restaurant, especially the server. He’s there to impress you, but he may still treat others around you with glimpses of his real character. Don’t let a guy get away with promising he would never disrespect you like that because you’re his woman. If he’s rude to the wait staff, he’s capable of treating you the same way in the future.

Fit mature couple warming up on the grass

4. Something that’s competitive.

There is a lot to learn from a fun and healthy competition. You want to know ahead of time that he’s okay with letting you shine. A guy who’s insistent on being at the top all the time may not be someone you want to be in a relationship with.

Why? Because he probably won’t see you at his level. He may also get jealous if you start getting more recognition and promotions at your job – or even earning a higher salary than him. If he’s too busy challenging you, he won’t be focused on connecting as a unit. In other words, get ready to lace up those bowling shoes and have some competitive fun.

5. Do something very simple.

It’s easy to enjoy yourself on a date that’s mostly set up for you to have a great time with each other. If you two wind up getting coupled up for real, then the dates may start becoming few and far in between, or at least with more at-home style dates. You want to know that he can still have a good time even if the dates are low-key or even stay-at-home dates.

So there you have it, ladies. These are the top five date ideas to get to know him better – dates that will allow you to test him to see if he is the right guy for a serious relationship down the road.

If you’re tired of going on fruitless dates you find on your own, perhaps it’s time to let our professional matchmakers here at Portland Single Dating Service do the hard work of dating for you. Let us do the searching, screening, and vetting for you so you can show up and enjoy meeting quality men who are fit to date and compatible with you. Let us introduce you to your Mr. Perfect.

To reserve your FREE (90-minute) matchmaking consultation, simply fill out the confidential form at the top of the page today!


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