After our third date, Alena and I continued seeing each other once or twice a week for a few months.  She lived in Maryland and I was in DC, so there were times that I stayed over her place, and she stayed over mine.  Alena, living on a teacher’s salary, lived in a dangerous, dicey area in Suitland, Maryland.  I would normally not visit that area late at night but when you’re in love, you take chances and do stuff that you normally don’t do.  We went food shopping together at the Pentagon City Costco in Virginia, and that always took up half the day since it was an exhausting three State shopping trip driving the food back to DC and Maryland.  When it got rainy and then snowy hauling all that food around, it was definitely an early test of our patience with each other. :-)

We went on a lot of different dates in the beginning, and after about the tenth date around the second month, we decided to make it official – like Facebook official.  Some of the most memorable dates we had early on were:
Dates from left to right: Madame Tussauds Wax Museum in Washington, DC, Dinner at Gordon Ramsay's Maze in New York City, Attending a taping of Who Wants to Be a Millionaire, National Portrait Gallery, Maroon 5 concert, First Trip together at Atlantic City during holiday break

Over the years, we also had a lot of fun, awesome get togethers with our family and friends:
Photos from left to right: Group mustache photo at Ocean City, John's 30th birthday at Banana Café, Dim Sum in NYC with parents, Japanese dinner at Tsunami Sushi, 2014 Halloween Party, masquerade ball, Medieval Times, Puerto Rico vacation, golf at Top Golf

Going from Dating Casually to Being in a Relationship

- Take one date at a time.  In the first few months of dating, it’s tempting to jump right into a relationship, but the best thing you can do is live in the moment and have a great time with the person you’re with.  Sooner or later, you’ll find out more about the person’s day to day lifestyle and what makes them tick.  And you’ll find out more about what you both love and want long term.  It’ll become clear to you both whether you should continue on being exclusive or call it quits. 

- It’s best to go on different dates and see that person in different contexts.  Anyone can seem attractive and interesting when you first meet them.  Most people don’t want to look bad in front of a stranger and is on their best behavior.  The important thing is to see how they react in all contexts – at home, at the grocery store, on a trip, when their exhausted or stressed, etc.  For me, there was no single epiphany that made me realize that Alena was someone I should commit to.  It was a series of hints and signs from our different dates that all gradually formed a picture that was clear – she had everything I was looking for, and nothing that was a real dealbreaker.

See if your date gets along with your close friends.  After several dates, when the time is right, have a group hangout with your date and close friends.  See if your date gets along with them.  Your trusted friends will tell you the truth on whether you two are good together.  And if you're invited to hang out with his or her friends, see if you get along with them.  It's not a perfect litmus test, but friends don't let friends date douchebags.

- Let’s talk about sex.  Every couple is different with sex.  Some couples have sex more often in the beginning and then it levels off to a regular amount.  Some couples decide to wait for months or if they’re really conservative, until marriage.  Some couples have sex frequently and keep that going.  My take on sex is that it can enhance a relationship or make it more complicated.  If a couple is finding out with each date that they have a lot in common, and are a match for each other, the sex only makes the relationship better.  If the couple finds out gradually that they are not a match, but are hooking up a lot, that makes it a bit more complicated to break up.  That’s why I’ve advocated in earlier blogs to not hook up too soon.  If things are going well, it’s good to flirt and make out in the first few dates and keep it romantic, but it’s best that both people have a good idea that there’s potential for something real before going all the way.  Also, for the ladies, if you wait a little bit it’s a way to test the guy’s patience to see if he’s really in it for you or for the sex.  Of course, none of this matters if both people are just looking for a fling.   
 
 
If you’ve reached the third date, that’s a great sign, because most people cut bait between date one and three.  The third date should feel more relaxed than the previous two dates.  Whereas in date one and two, there is a bit of pressure going into it and concerns about making a mistake, date three is more about getting to know each other better without the need for a fancy night out.  I think date three is a good time to invite that person over, or to go over their place. 
This was the first dinner that Alena made for me.

For our third date, we spent it at my place enjoying dinner and a movie.  Alena knew the way to my heart was through my stomach, and she brought over a delicious dinner of sautéed shrimp, salad, a mix of sweet and regular baked potatoes, and some tomatoes with mozzarella cheese.  That was the first time someone that I dated cooked me dinner, and it was a sign to me that she was a keeper, because she was putting in the effort too.  The same night, she looked at my fridge, saw that I had healthy food in there, and told me months later that it got me some points, since I was walking the walk about eating healthy, not just talking the talk like other guys did.

Before the Third Date

- Keep your options open.  Before the third date, I think it is fair game to keep your options open and date other people casually if you haven’t committed to dating anyone exclusive.  It’s not about being a player – it’s about dating efficiently.  It's about giving yourself as many options as possible in case something doesn’t work out, and not making the mistake of going too fast with anyone too soon.  The first or second date can be unpredictable.  The person you’re dating may be dating someone else casually, and may be gone tomorrow.  It’s good to be dating someone else casually if possible so you don’t put all your eggs in one basket too soon, and you don’t get too head over heels for someone, which can scare them away. 

But I caution about keeping the options open too far into the distance – after three or more dates, you should have a better sense of who is a better fit, and you should respectfully narrow the dates down.

- Rejection is likely to happen.  You’ll find as you go on more dates, most of them end before date three.  It’s normal and happens to everyone, and although it can sting after a while of going through it over and over again, just move on and take whatever lessons you can draw from them.  Write the experience down in a dating journal.  Rejection sucks, but I can assure you that it’ll pass, and when you meet the right person, you’ll look back and may even feel like you dodged a bullet!