Talk to her in person. Heart-to-hearts always are better in person. Set up a time for the two of you to get together. Have coffee or go shopping. In the midst of casual conversation and getting updated on what is new in her life, you will have the opportunity to ask about her love life. Listen for clues. Is she saddened by her singleness? Has the Big Breakup from two years ago caused her to fear dating again? Is she discouraged? By first listening to your sister, you will be able to help her make positive changes that will allay any fears.
Think of dating as "making new friends." Often women who are skittish about dating really are just afraid of the pressure the term creates. Remind her that going on a date doesn't mean she is headed to the chapel anytime soon. If she's been hurt by a past relationship, perhaps she is afraid the same ending will befall any new dating experiences. Remind her that going on a date is like spending quality time with a new friend. That may relieve some of the fear and pressure and help her to relax.
Set her up. Dating usually doesn't happen unless someone facilitates the date. That facilitator may have to be you. Some women feel awkward about creating dating opportunities for themselves--such as asking a man out or trying out online dating services like eHarmony or Match.com. Additionally, the post-modern dating culture doesn't guarantee a guy will make the first move. You should return to the Jane Austen-era of matchmakers and become one for your sister. Think of quality, eligible men that might be a good match for her. A kind plea: Don't set her up with someone just because he is single. You are her sister, and hopefully you know her quite well. Use that to your--and her--advantage.
Affirm her attributes. It's hard to take that deep breath and enter the scary, vulnerable world of dating. Help her gain confidence by reminding your sister why she is so wonderful. Hearing words of encouragement does have the power to change the way she feels about herself. Remind her that no matter what happens on any one date, that she still is a beautiful, smart and valued woman.
- Many singles are staying friends longer and getting married later. In 2008, the average age for first-time grooms is 27.4, while the average age for first-time brides is 25.6, according to a U.S. Census report.