How to Win at Online Dating

Rachel Yerks

Photo by Mark Rivera on Unsplash

For background, after a year of casually looking, I found my partner on OkCupid. My partner and I have been dating for 2.5 years and live together in a small apartment with our cat. I could not be happier with my relationship. Here’s how he stood out in a sea of profiles.

Pick a time and place to have a date

Sounds simple, but anyone who has used dating apps knows it’s hard to get a date. People end up texting forever and never meet up, or when they do meet up everything to talk about on the date has already been discussed virtually.

By proposing a date within the first two weeks of talking, he made sure we would have something to talk about when we met. Our topics weren’t exhausted by continuous texting, and we had an exciting discussion to look forward to. He told me exactly what days he was available and what towns he could drive to so I would feel comfortable and could pick the location.

Some women won’t be comfortable going on evening dates, but if you are, that’s great. When he suggested an evening date, I declined and stated safety as a reason, and he was more than willing to meet for an afternoon coffee and ice cream instead. Our date eventually did lead into the early evening with us getting dinner, but I was still happily home before dark. Be flexible with your timing, without sacrificing safety.

Side note: Safety may not be a huge concern for you, or for people in your area of the country, but for others, it is a very real concern. Please be considerate of those concerns when using dating platforms. You will get more dates by being courteous.

Make your priorities known

My partner dated a college student previously. He turned down better job offers to take a job close to her school to be with her, and she broke up with him a couple of months later. He stated that work was his priority and he would be moving out of the area if any job offers arose. He would not make the mistake of putting a relationship before his career again.

When he moved away six months later, I expected it and was prepared. I continued my college education and after I graduated, I moved to be with him. As an unemployed individual hoping to freelance online, it didn’t matter where I was. I am happy with my decision, and since our relationship is more serious now, he has agreed to take his next position on the east coast which is where I want to end up.

Know what you want going into the relationship, and stick to it. There will be plenty of other areas later in your relationship to compromise on. Don’t compromise on what’s really important to you and your partner. In our cases, my partner prides himself on his career and I pride myself on my flexibility. It's a win-win.

Split the check 50/50

I don’t believe in being paid for. For some, it’s a nice gesture, but for others it makes them feel obligated like they owe the other person for something. Yes, he pays for date nights now and then, but our first date was split down the middle. I didn’t want to have that feeling of obligation, and he had been put in positions on first dates where he paid for his date’s far more expensive meal.

By splitting 50/50, you are keeping the power in the relationship equal. One person doesn’t feel like they’re being used, and the other person doesn’t feel like they have to make up for anything. A date is a treat for both of you, and both of you should pay for it accordingly, in my book.

This advice goes out the window when you’ve been together for a few years. You know your partner better and no one on either side will feel uncomfortable about being paid for because it will even out in some way or another. You can be [mostly] confident your date won’t disappear the day after your expensive dinner.

Set up another date immediately

If you had a good time on your first date, don’t play hard to get. You don’t have enough leverage to do that after one date. Plus, it’s crappy. Tell the other person you had a nice time at the end of the date. If they say they also had a nice time and ask to see you again, agree and let them know you’ll text them with some days you’re available.

Make sure to text them later that night, or the next day. Think about how you would want to be treated. If you were excited about a reply and didn’t get one for two days, how would you feel about that other person? In my case, at the end of our date, my partner stated he had a nice time and if I was interested in having another date to let me know. I agreed to let him know and went home.

After a couple of hours of relaxing at home and thinking about the date, I texted him and said I also had a good time and if he’d like to meet up again to let me know. He texted back a few minutes later and asked when was good for me. Neither of us was interested in playing hard to get, which isn’t really appropriate in a brand-new relationship.

I really have a fantastic relationship. My friends call my partner ‘the unicorn’ of online dating, as in how did I get so lucky? The above steps are why he stood out to me in a sea of other profiles. I actually stopped talking to other people on OkCupid after my second date with my partner because I was confident we were headed in the right direction. You don’t have to commit that early of course, but if it feels like the right step for you, take it, regardless of what others think. You don’t need to ‘play the field’ if you don’t want to.

If one date doesn’t work out for you, remember there are plenty of fish in the sea. Don’t continue to go out with someone after you’ve broken up in the past. You deserve better, and by looking for green flags and putting yourself first, you will find your dream relationship. It just might take a while.

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Owings Mills, MD

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