Depending upon your point of view, dating is either easier or harder as you get older. But how old do you have to get until it really gets easy? After all, you are now an adult. Teenage angst is behind you. You are older, more experienced and possibly wiser and wealthier. Theoretically, life should be easier, but here you are, back at the start. You are single, wondering how to ask that woman, girl, female person out on a first date.

Now, before you let your stomach become tied up in knots or, worse still, go into avoidance mode, take a deep breath. Next, grab a pen and paper, sit at the computer or cuddle up with some other familiar list-making device. We are about to talk strategy here. You are about to prepare yourself for battle.

Yes, even before you pop the question, you need to block-out a campaign. If nothing else, it will help calm your nerves. It will also clarify whether you are ready for this next step.

Considering The Target

The very first thing you need to look at is availability of your target. In this day and age, it is always a good thing to discover such things out in advance.

• Is she available?
• Does she already have a boyfriend?
• What is her situation?
• Is she even interested in men?

If you are in everyday or even infrequent contact with her, this should not be a very difficult task. Consider any, and all, interaction the two of you have had.

• Did she seem interested at all in what you had to say?
• Was there an obvious attraction?
• What body language did she express?
• Did she stand close or step back? If she stood as far away from you as possible, you may have to discard her as your primary target.
• Where did the meetings take place?

You always have to put things into context. Doing so will help prevent you from becoming self-deluded. This, you have to avoid at all costs. Do not “read into” the comments or situations things that are not really there. If you have any doubts, ask a good friend. If you know any mutual friends, this can really help clarify her situation.

Next, you should consider the content of these conversations.

• Were there any indicators from her or anyone else there of particular interests?
• Did she mention specific groups or types of music she liked?
• Is she an opera fan or does she prefer rap?
• Did movies come up?
• If so, what genre?
• Is she fond of video games or did she say she liked hiking, swimming, mountain bike riding or any other outdoor activity?
• Is she the kind of girl who reads, paints or writes in her spare time or for a living?
• Does she like to go out or stay home?
• Does she prefer clubbing or quiet jazz or folk clubs?
• Is she a group person or does she prefer to be alone?

Putting together what she said and where she said it, can help you in a number of ways. It may determine whether she will be receptive. Just as important, it will help you to discover whether the two of you have anything or anyone in common. It will also give you an indication of where you can go and what you can do on your first date. Knowing this information, you can begin planning and preparation for asking her out.

Prior Preparation For The Date

Are You Physically Ready?

There are various ways to ensure you are physically ready for that first or any other date. It is all about personal hygiene. You need to look your very best. At the same time, you should not overdo it. If you are a casual kind of guy, do not appear all duded up. If you tend to dress up, do not dress down. This is particularly true if the woman you are about to ask out already knows you. This also applies to the situation. If you are going to ask her out at work, you need to dress accordingly.

What is important here is the overall presentation. No matter what you are wearing, you and it must be clean. Wash your hair, style it if need be, scrub yourself clean. If you shave, do so without cuts and nicks. If you do not, make sure your beard or mustache is clean and trimmed. These are superficial, but people still judge a book, initially, by its cover.

The same rational applies to your clothes. They must be clean and fit properly. You should smell nice but not overpoweringly so. Some women do not want to go out with a man who smells prettier than they do. There is also the case of allergies. Does your potential date have any? You do not stand much of a chance if she ends up sneezing when you try to ask her out.

Two Approaches to Ask A Girl Out 

There are two basic approaches to ask a girl out – direct or indirect. There are proponents for both styles. In fact, each does have its specific merits and appeals as well as its drawbacks. You need to know your own confidence level, your ability and preference. You also need to be aware of the woman’s position. Will a direct approach work? Is it better to be open-ended or indirect?

The direct approach is simple. You go up to the woman, hopefully alone (if not, take her aside casually) and ask if she wants to go out a weekday, Saturday, Sunday afternoon, evening or morning to such and such event. At its most basic, the direct approach is, well, direct. It is straightforward. It states simply and effectively your intention. You want to go out with so-and-so to such-and-such a place on such-and-such a date. You can say it all at once and get a reply. You can get it over with quickly.

With the direct approach, your intentions are crystal clear. It can be very effective on some women and for some occasions. On the other hand, when it falls flat, it sinks into the floor and heads for the basement. This is because the direct approach leaves no wriggle room. It does not allow for consideration or graceful opting out. It is an all-or-none tactic. You generally get a yes or a no. Sometimes, you may get a “let me think about it.” This is not a good sign.

The indirect approach is less, well, direct. This method allows both of you the chance to be graceful in either acceptance or rejection. It also makes alternatives available. It is open-ended and clearly indicates interest. You may not provide a specific date or even event. You may simply indicate your interest and leave it up to her to reciprocate or not. A problem is you may not resolve your interest.

The following are examples of both methods:

• Hi! How would you like to get together sometime? Indirect.
• I’m planning to go see/attend/visit _____this week. Are you interested in coming with me? Direct
• I have tickets to see ______, care to join me? Direct and indirect.
• Would you like to go out to dinner/the movies/a concert next week? Direct.
• I’m having several people from ____ and some friends over for a get together/football game/the Oscars etc. this/next weekend. Care to join us? Indirect.
• Is it true you really enjoy ballroom dancing, salsa, Monty Python, Chagall, this group/ this performer, etc.? I have tickets to this show/concert/ exhibit etc. Would you care to join me? Indirect and Direct.
• Several of us are going to ____? Care to join us? Indirect.
• Would you like to play tennis/golf etc. with me some day next week? Direct.
  Maybe we could get together for a drink/coffee some time. Indirect.
• I’ve heard you like Westerns or Alfred Hitchcock or foreign films? So do I. Next week, ____ is holding a marathon. Care to join me? Indirect.
• I want to try ___. I hear you’re an expert. Could you teach me? Indirect.

Other Factors

The two approaches differ, but you can combine them. What you also need to consider is how you are going to initiate the event. Do you corner her? Do you approach her at work/exercise/event, as she is leaving work, the event, etc.? You will have to rely on your own assessment of the situation. It may be taboo to ask her at work, but you may be able to do so at lunch or a coffee break. When she is working out at the gym, you may not want to interfere with her routine. Perhaps, you can talk to her during her break, or as she is getting ready to leave.

There is also the phone and e-mail or instant messenger. The phone is easier for some. It is convenient and allows them to relax. You can have a script ready from which to read. It is also impersonal. Save the phone as a follow up unless it is pre- arranged. As for text messages and other forms of electronic communication – this is appropriate if this is how you met. If you meet on-line, naturally, you can ask her on-line. If you see her in person, it is better to ask her in person. You may, however, use the internet to contact her to arrange a meeting to ask her out. With some busy people, this may be the only way you can do so.

Whether you decide to talk to her before, in the middle of something or afterwards is up to you. This is a personal call. What you should do, for your sake and hers, is to ask her out when she is alone. It is usually difficult and embarrassing to ask someone if they are with a bunch of people. This is particularly true if she turns you down or responds negatively.

Are You Ready When The Big Day Arrives?

You are groomed and prepped for the event. In a few minutes or hours, you will be back in the dating game, you hope. Here are a few more tips to consider.

• Be assertive but not aggressive in your approach. Do not come on like barnstormers.
• Be confident but not cocky.
• Relax.
• Be real. Most women can spot a phony a mile away.
• Do not make this seem like the fate of the world lies in the balance. It is a date, not the be-all and end-all.
• Listen carefully to what you are saying.
• Listen even more carefully to what she replies.
• Consider it a learning process. You have not dated in a long or even longer time.
• If she says, “Yes,” celebrate quietly. Say great or something similar than go back to work, play, etc.
• If she rejects you, do not take it to heart. As the book says, “She’s just not into you.” It is better to find that out now than later. Look at it as an experience, a trial run. Practice will make perfect IF you learn from it.

With the first effort over, no matter how it goes, you have begun the first steps back into a relationship with the opposite sex. Your first date may turn out to be fun, boring, or even a disaster. Whatever the outcome, it marks the first of many forays into the sometimes crazy, but never dull, world of dating.