How to Get Comfortable on Dates Again When It’s Been a While

After three years of more or less random celibacy, I vowed to go on two dates a week, every week. I’m not a psychologist, but at the moment I’m pretty much an expert on first dates. And (so as not to brag), but I am usually asked again.

During the three years I hadn’t pursued romantic or sexual encounters, I actually had the idea of ​​what dating would be like if I tried again. After I wrote about what it means to be lonely for a long period of time, I received a huge response in emails, comments, and tweets that indicate that this is a fairly common problem. If you haven’t been dating for a long time, it is difficult to get back on the horse. In fact, you are almost certain that the horse will fight you. Maybe you’ve just ended a long-term relationship, or maybe you didn’t want to leave the house. If you really want to go back there, here are some of my observations after meeting nearly a hundred new potential soulmates.

Go on a lot of dates!

Full Disclosure: I went on dates during these three years of celibacy. Maybe four times. Because I met people so rarely, I put tremendous pressure on myself and my date. I was incredibly disappointed when they didn’t go well or lead to more. These bad feelings kept me from trying again for a long time. After forcing myself to immediately brush it off and go on another date, I found that bad dates are just statistical probabilities. One bad date doesn’t mean good isn’t waiting around the corner, and the more you go on, the less upset when they’re first.

Dating apps are good

Oh, do you hate dating apps? Hard. Yes, you may be in love with someone who also silently works on their laptop in your coffee shop, but do you know if they are single? Do you know if they are interested? If you try asking them and they say no, are there hundreds of other people standing right behind them who are alone and potentially interested? Dating apps are an extremely effective way to meet many people who also want to date. Upload them all, update your photos, CVs, and substantive conversations. You can meet someone organically in real life, but the first date with them will go a lot better if you practice.

Ask people

Even though I spent a lot of time on the apps, in the end I got up the courage to ask people I knew in real life. No coworkers, no ex-best friends, or anyone else with whom this could cause problems. Just people I thought were nice and interesting. Some said no, which helped me learn how to deal with people normally after rejection. But some said yes and we had great dates. While it didn’t lead to a relationship, those dates didn’t ruin our friendship either. And when you know someone, you can miss a lot of small talk, what are the rules.

Set dates near your home

Look, this might sound lazy, but when you’re back in the dating world, it’s just better to try and meet people in a place that’s convenient for you. Meet after work outside your office, at your local bar, or anywhere less than three train stops away (NO TRANSFER). When things go wrong, you only spend an hour drinking, not three hours drinking and an epic commute. It seems a lot more manageable. And if all goes well, you can invite them straight to your home …

Bring cash for at least one drink

It is helpful to have enough cash on hand to pay for drinks. Most bars have minimum cards and you may not need to stop for number two. It will also help you avoid the awkwardness of who is paying for what. I personally enjoy paying for my drinks on the first date and it’s nice to skip any negotiation or confusion about this by just omitting those bills.

Try a date with coffee

I used to avoid meeting people in bright daylight when drinking a gut-stimulating drink, but now I am a convert. Get lost in the discomfort of talking to a stranger and do it under the influence of caffeine. Getting to know someone sober is good because you will remember it. Coffee dates also relieve some of the sexiness of the situation, which is great if you’re not just looking for dating. And if someone makes you laugh when you’re not drunk, that’s a very promising sign. Plus, coffee is much cheaper than alcohol.

Wear clothes that make you feel good

Since you are saving so much money on these coffee dates, buy some outfits that make you feel pretty. Obviously I wanted to look sexy when I started dating again. But my sexy wardrobe is outdated. It made dating preparation stressful because nothing suited me and made me feel good about my cool body. As soon as I bought a couple of simple tops and dresses that I could just throw on, feeling good about the way I look became easier. Who knows if dating thought I looked cool; but at least they weren’t interested in why I was constantly fidgeting.

Don’t do what you don’t want to

One day at the end of a very unfortunate date, I held out my hand to someone to say goodbye. He was upset, saying that the handshake was strange, so I hugged him. On the way home, I felt disgusting. It was just a hug! Not so important! But I didn’t want to hug him, and I shouldn’t have. Remember how comfortable you are with these things, and know that it’s perfectly okay to turn down any offers, requests to meet again, or insistent requests to stay and have another drink. There is usually no reason to be rude on dates, but definitely don’t be rude to yourself! Respect your time and your personality; if someone makes you uncomfortable, leave.

Remember, your date is probably not right.

Going out on a date with the idea that you’re going to meet a soul mate is always frustrating, and it’s not because people are actually shittier than in your head. This is because you exhibit many ideas about who they are and who they will be to you, instead of really getting to know them. The dream of finding the One is sweet. Making a real connection with another person is more enjoyable.

Also remember that your date wants you to please.

Many people lose their temper, thinking that their date will notice every enlarged pore on their face, or think their voice sounds weird, or wonder why they are wearing mismatched socks. If someone shows up to meet you, suppose they are very eager to meet someone they like and are looking for your positives. Take advantage of meeting someone who is also trying to impress you.

Be yourself

When my mom told me to be myself, I wanted to kill her. I myself every day and I don’t win any awards. But now I understand what she meant. Being yourself doesn’t necessarily make people like me, but it does make me like me. I do things that make me feel strong and cool when I’m not dating, so I can bring that energy with me on a date. Fill your life with the things you love, so when you date someone, they make you the happiest and most satisfied. It is very attractive.

You can read more about Amy’s permission on her 2 Dates a Week blog .


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