Dating Can be Challenging, Regardless of Your Age or Experience

Dear Neil: Could you explain how dating works? I am 29 years old, and don’t know how to tell a guy that I want him to invite me out on a date. I get routinely texted to hang out with a guy and his friends, but I don’t want to just hookup with guys anymore. I’m looking for a serious relationship. How do I get out of the hookup culture I’m in?

Befuddled in Seattle

Dear Befuddled: The hookup culture so popular with the millennial generation (ages 13-33), has by some accounts taken the word “date” out of the vocabulary. Instead of dating, a fairly sizable number of millennials are involved in a cycle of text messaging such as: “I’m at Joe’s Pub with some friends of mine from college. Want to meet up for a drink or something?” or “Hey, anything fun happening tonight?”

Often they are last minute spontaneous invitations to tag along. They are most commonly commitment-free, and often become short-term romantic flings, especially when alcohol or other substances are used. A fair number of millennials have never been out on a traditional date, and it leaves some of them to wonder how to attract an actual boyfriend or girlfriend.

This is complicated by the fact that many millennials don’t know how to get out of the hookup culture as you so well described, and don’t have much of a clue about the mechanics of a traditional date: how to invite someone out on one, what to do on a date, what you talk about and so on. In fact, on a variety of college campuses, (Colorado State in Fort Collins and Boston College to name two), classes on Dating 101 are offered so students can learn how to plan, execute and succeed on a traditional date.

It is easier to hookup than it is to ask someone out on a date. Asking someone out on a date requires courage and risk. Spontaneous texting is more risk-free: if one lady says she has plans, you just go on to a second lady, and then a third, until you find one that wants something to do. And since hooking up commonly leads to casual sex without a lot of expectations, you can see its obvious appeal—and its just as obvious drawbacks.

Chief amongst the drawbacks is that you are not actually in a real relationship, so your feelings and emotions must be held in check, and it’s harder to know how to behave in a relationship, let alone have realistic dreams of a future together.

My advice to you is to simply hold out for what you want. You can say “no” to texts inviting you to casually hang out in a group, and you can say “no” to hooking up. You can let every guy who wants to be with you know that you will only accept invitations to go out on a date—such as movies, plays, dinners or dancing, to name a few possible activities. You can also refuse to accept spontaneous invitations, telling a guy that you need a minimum of three days notice, so he has to put some foresight, planning and effort into it.

If a guy wants you, make him work for it, and don’t accept anything less.

Dear Neil: I have been married for 35 years, but am now in the process of divorce. Since my high school sweetheart became my wife, she is the only person I’ve really been with, and I’m finding that dating is a lot harder than I thought. Do you have any suggestions about how to get back into things?

Shy in Colorado

Dear Shy: First, make sure you clean up your own emotional baggage from your marriage so you are able to freely give your heart to another. You don’t want to charge your next partner a price for the disappointments, battles or struggles you have been through with your soon-to-be ex-wife.

Second, go to where people have the opportunity of talking or interacting with each other, such as an adult education class, a tennis clinic, a photography class, a travel show or a dance class, to name a few. Third, explore new things you would be interested in experimenting with or trying, and then find groups, organizations or classes that do the activities you’re interested in. You will discover whole new groups of people.

Forth, connecting online has become the top place where single, available people are meeting each other these days. Describe yourself in some detail on one of the many matchmaking sites. What do you enjoy? What is unique or different about you that someone else might find interesting or amusing? Post good current photos of yourself, with at least one being a close-up face shot and at least one being a full-body shot. Then, search around and invite everyone who interests you to get together.

Finally, introduce yourself to someone who attracts you who is also available. You risk being rejected, but you also give yourself an opportunity to be successful.

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